Chapter 3: Atmosphere chemistry application · Chapter 3: Atmosphere chemistry application 66 3.2.2 Sulphuric acid-catalysed formation of hemiacetal from glyoxal and ethanol Presentation

Chapter 3 Atmosphere chemistry application

61

32 Series of papers


62

321 A computational investigation of the sulphuric acid catalysed 14-hydrogen transfer in higher Criegee intermediates

Presentation of the article

TitleA computational investigation of the sulphuric acid catalysed 14-hydrogen transfer in higher Criegee intermediates

Authors Sarrami F Mackenzie Rae FA and Karton A

Journal International Journal of Quantum Chemistry 2018 118 e25599

DOI httpsdxdoiorg 101002qua25599 Date of Publication February 2018

Graphical TOC

63

58

59

60

61

62

63

64

65


66

322 Sulphuric acid-catalysed formation of hemiacetal from glyoxal and ethanol


Title Sulphuric acid-catalysed formation of hemiacetal from glyoxal and ethanol

Authors Sarrami F Yu LJ Wan W and Karton A

Journal Chemical Physics Letter 2017 675 27-34

DOI httpsdxdoiorg 101016jcplett201702084 Date of Publication March 2017

Graphical TOC

67

68

69

70

71

72

73

74

Chapter 4 Thermochemistry of icosahedral closo-dicarboranes

75

Chapter 4 Thermochemistry of icosahedral closo-dicarboranes 41 Introduction

Boron like carbon forms stable covalently bonded molecular frameworks

through self-bonding a typical example being polyhedral cluster structures

possessing a unique stereochemistry Polyhedral heteroboranes have been the subject

of intense research for over 55 years 231232233234235 A subset of this extensive class

of compounds is dicarba-closo-dodeca-boranes commonly referred to as carboranes

(an abbreviation of the IPUAC name carbaboranes) having the general formula

C2B10H12

Carborane clusters were first reported in the 1960s and since then this area has

experienced enormous growth Many new synthetic procedures have been

developed236237238239240241 The synthetic advances bonding theories of boron

clusters and more specifically icosahedral carborane derivatives have been utilized 242243 in such diverse areas244 as medicine (including boron neutron capture therapy

and drug delivery) catalysis nonlinear optical materials liquid crystals metal-ion

extraction super acid chemistry 245 conducting organic polymers coordination

polymers and others


76

411 Introduction to Thermochemistry of icosahedral

closo-dicarboranes

Highest members of this class of compounds are dicarba-closo-dodecaboranes

commonly referred to as carboranes (an abbreviation of the IPUAC name carbaboranes)

having the general formula C2B10H12 Carboranes exist as (1) ortho meta (2) and (3)

para isomers which differ in the relative positions of the carbon atoms in the cluster

The structures of the three isomers for carborane are shown in Figure 41 The clusters

have nearly icosahedral geometry in which each of the carbon and boron atoms are

hexacoordinate

Figure 41 ortho (1) meta (2) and (3) para-Carborane

The synthesis of ortho-carborane was first reported in 1963 by two groups246247

Ortho-carboranes are prepared by the reaction of acetylenes including both mono and

substituted alkynes with B10H12L2 which is generated from decaborane (B10H14) and a

weak Lewis base (L= CH3CN RSR R3N) The meta and para-carborane isomers are

prepared by thermal isomerization of ortho-carborane under an inert atmosphere At

400ndash500 degC orthondashcarborane converts to the meta-isomer which in turn rearranges to

the para-isomer between 600ndash700degC The mechanism of isomerization has been the

subject of considerable interest248249250251252 The structural properties of such species

are still not clearly understood especially for systems comprising large clusters which

are not always amenable from direct structural investigations such as those utilizing X-

ray and electron diffraction techniques There have been only a small number of

correlated ab initio investigations of their thermochemical properties


77

One of the goals of the present paper was to re-evaluate the stability of the

icosahedral dicarborane isomers their ionization potentials (IPs) and the various CndashH

and BndashH BDEs by using the high-level ab initio W1ndashF12 thermochemical protocol

W1ndashF12 is a high-level composite theory that obtains the all-electron relativistic

CCSD(T)CBS energy (complete basis-set-limit coupled cluster with singles doubles

and quasi perturbative triple excitations) and achieves an accuracy in the sub-kcal molndash1

range for molecules that have wave functions dominated by dynamical correlation We

obtained heats of formation (

isomerization energies ionization potentials and CndashH and BndashH bond dissociation

energies for the carborane isomers using the high-level ab initio W1ndashF12

thermochemical protocol To the best of our knowledge the thermochemical properties

of the carboranes have not been previously studied at the CCSD(T)CBS level of theory

Thus this investigation provides the most accurate thermochemical values that are

presently available for these compounds Our best W1ndashF12 heats of formation

According to these W1ndashF12 values the meta isomer is less stable than the para isomer

by 269 kcal molndash1 whereas the ortho isomer is less stable than the para isomer by 1865

kcal molndash1 These isomerization energies are in reasonably good agreement with

previous theoretical values obtained at much lower levels of theory Finally we

evaluated the performance of a range of lower cost Gn and CBS composite ab initio

procedures We found that the G3(MP2)B3 procedure offers a stellar pricendashperformance

ratio with an overall RMSD of only 027 kcal molndash1


78

412 Thermochemistry of icosahedral closo-dicarboranes a composite ab initio quantum-chemical perspective


Title Thermochemistry of icosahedral closo-dicarboranes a composite ab initio quantum-chemical perspective

Authors Sarrami F Yu LJ and Karton A

Journal Canadian Journal of Chemistry 2016 94 1082-1089

DOI httpsdxdoiorg101139cjc-2016-0272 Date of Publication July 2016

79

80

82

83

84

85

86

Chapter 6 Appendices

87

Chapter 5 Summary and Conclusions

This thesis examined the applications of high-level computational methods for a

range of important thermochemical and kinetic properties in organic and

biochemistry The dissertation has covered various theoretical procedures (eg ab

initio methods DFT methods and composite methods) to study specific reaction

mechanism based on 1) antioxidant activity of carnosine and vitamin E and

designing more effective candidates 2) catalytic reaction related to the atmosphere

and 3) calculation of thermochemical and kinetic properties (eg different type of

data set for isomerization energies reaction energies and their barrier heights) This

combination of these approaches gives a more in-depth understanding of the

application of high-level computational methods in chemistry biochemistry and

atmospheric chemistry A brief summary for the research presented along is

provided

Computational anti-oxidant design based on carnosin was the first project we

investigated by studying the reaction of intramolecular Br+ shift in carnosine that

from the imidazole ring and primary amine moieties The Br+ transfer is found to be

the rate-determining step with a barrier of 972 kJ molndash1 relative to the minimum-

energy conformation of N-brominated carnosine Based on that results we started to

design new candidates by first) increasing the length of the β-alanyl-glycyl side-

chain for Br+ shifts (structural effect) and second) substitution of the imidazole ring

with some electron donator and acceptor groups for both the Cl+ and Br+ shifts

(electronic effect) In addition we showed that combination of structural and

electronic effects leads to the most effective candidate For example a derivative of

carnosine in which the length of the β-alanyl-glycyl side chain is increased by one

carbon and the imidazole ring situated with a strong electron-donating group results

in barriers of 414 and 278 kJ molndash1 respectively for the Cl+ and Br+ transfers


88

In another project we investigated the mechanism for the intramolecular ring-

opening reaction of a-tocopherone (as a part of antioxidant activity mechanism of

vitamin E) using DHDFT method The uncatalysed reaction is associated with a

high activation enthalpy of 1599 kJ mol-1 Involvement of one and two water

catalysts in the TS reduce the reaction barrier height to 1273 and 1103 kJ molndash1

respectively This catalytic efficiency can be rationalised by (i) the reduction in

strain energy in the TSs in the order uncatalysed 1-water catalysed and 2-water

catalysed and (ii) improved trajectories for the proton transfers from the

hydroxyl group to the heterocyclic oxygen This catalytic effect can be

explained by reducing the strain energy from uncatalyst to 2-water catalysed

which improves the proton transfer from hydroxyl group to heterocyclic oxygen

Based on proposed mechanism we continued to explore new potential candidate

by reducing the size of heterocyclic ring and replacing the heterocyclic oxygen

by sulfur atom Our results showed that reducing the size of the heterocyclic ring

of the a-tocopherone to a four-membered ring not only reduces the barrier for

the ring-opening reaction but also significantly increases the thermodynamic

driving force for the overall reaction In particular for the four-membered ring

analogue of a-tocopherol we obtained reaction barrier heights of 892 and 873

kJ mol-1 for the reactions catalysed by one and two water molecules

respectively We hope that our computational investigation will inspire further

experimental investigations of the antioxidant activity of the proposed antioxidants

In the second part of this thesis we investigated the application of high-level

computational methods for two important catalytic atmospheric reaction mechanisms

including 1) sulphuric acid-catalysed 14-hydrogen transfer in higher Criegee

intermediates (CIs) and 2) sulphuric acid-catalysed formation of hemiacetal from

glyoxal and ethanol In the first project Using the high-level G4(MP2) composite ab

initio theoretical procedure sulphuric acid was found to effectively catalyse 14

hydrogen shift reactions in methyl CI and in isoprene derived and a-pinene derived

CIs These products formed through this channel are likely to directly contribute to

organic aerosol production Conversely water was found to exhibit only a minor

catalytic effect for these 14 H-shift reactions The reaction barrier heights for the

sulphuric acid-catalysed reactions are 164 (methyl CI) 245 (isoprene CI) and 84


89

(a-pinene CI) kJ molndash1 relative to the reactant complexes in comparing to the

uncatalyst reaction 722 (methyl CI) 805 (isoprene CI) and 662 (a-pinene CI) kJ

molndash1 of respectively Therefore the computational findings presented here suggest

the possibility of a facile bimolecular reaction of sulphuric acid with higher Criegee

intermediates containing a β-hydrogen resulting in the formation of vinyl

hydroperoxide Reaction with sulphuric acid is therefore likely an important

removal process for stabilized CIs in regions of high H2SO4 concentrations

In the second project of this chapter we used the high-level (G4(MP2)

composite ab initio procedure to investigate the uncatalysed water-catalysed

ethanol-catalysed HC(O)OH-catalysed and H2SO4-catalysed reactions of glyoxal

with two consecutive ethanol molecules to form a hemiacetal in the first step and a

dihemiacetal in the second step Introduction of a water molecule reduces the

reaction barrier for the first step by converting the strained 4-membered cyclic TS to

less strained 6-membered cyclic TS In particular we obtained an activation energy

of = 873 kJ molndash1 relative to the RC1 for water-catalysed reaction A formic acid

catalyst reduces the barrier for this reaction to 330 kJ molndash1 relative to RC1 This

significant reduction in the activation enthalpy is attributed to the conversion of the

6-membered ring TS to an 8-membered ring TS An H2SO4 catalyst further reduces

the barrier for this step to merely 163 kJ molndash1 relative to RC1 This reduction in the

activation enthalpy is attributed to the further reduction in strain energy associated

with moving from a first-row central atom to a larger second-row central atom in the

oxoacid This work shows that H2SO4 can also effectively catalyse an intermolecular

proton transfer that is coupled with the formation of a covalent CndashO bond These

findings may have significant consequences for atmospheric models since the

conversion of glyoxal to hemiacetal in the atmosphere may have important

consequences for secondary organic aerosol formation under atmospheric conditions

In the last part of my thesis we obtained heats of formation isomerization

energies ionization potentials and CndashH and BndashH bond dissociation energies for the

carborane isomers using the high-level W1ndashF12 thermochemical protocol To the

best of our knowledge the thermochemical properties of the carboranes have not

been previously studied at the CCSD(T)CBS level of theory Our best heats of

formation values are ndash5063 kcal molndash1(para-carborane) ndash4794 kcal molndash1


90

(metacarborane) and ndash3197 kcal molndash1 (ortho-carborane) According to these W1ndash

F12 values the meta isomer is less stable than the para isomer by 269 kcal molndash1

whereas the ortho isomer is less stable than the para isomer by 1865 kcal molndash1

These isomerization energies are in reasonably good agreement with previous

theoretical values obtained at much lower levels of theory These values agree with

the experimental values adopted by the NIST Chemistry Web Book to within

overlapping uncertainties however they suggest that the experimental IPs represent

underestimations Finally we evaluated the performance of a range of lower cost Gn

and CBS composite ab initio procedures We found that the G3(MP2)B3 procedure

offers a stellar pricendashperformance ratio with an overall RMSD of only 027 kcal

molndash1 for the isomerization ionization and bond dissociation energies However the

more recent G4-type procedures provide relatively poor performance with RMSDs

of 369 kcal molndash1 (G4(MP2)) 204 kcal molndash1 (G4) and 125 kcal molndash1 (G4(MP2)ndash

6X)

Although the high-level computational methods in this thesis are highly accurate

there are some limitations that have to be mentioned

1) When modelling biological systems (Chapter 2) we use simplified models in

which solvent and pH effects are treated in an approximate way (for example

with a continuum solvent model) In future work it would be good to

perform extensive Molecular Dynamic (MD) simulation to model these

effects more accurately

2) In the atmospheric catalytic reactions considered in Chapter 3 the reaction

barrier heights and the catalytic enhancements are calculated using classical

transition state theory and tunneling effects are completely neglected In

future work it would be good to convert our accurate reaction barrier heights

into reaction rates using master equation and RRKM methods with explicit

account of tunneling effects


91


61 Appendix A Online Supplementary Information for ldquo Thermochemistry of icosahedral closo-

dicarboranes a composite ab initio quantum-chemical perspectiverdquo by Sarrami F

Yu LJ and Karton A Canadian Journal of Chemistry 2016 94 1082-1089

62 Appendix B Online Supplementary Information for ldquo Sulphuric acid-catalysed formation of

hemiacetal from glyoxal and ethanolrdquo by Sarrami F Yu LJ Wan W and

Karton A Chemical Physics Letters 2017 675 27-34

63 Appendix C Online Supplementary Information for ldquo Computational design of bio-inspired

carnosine-based HOBr antioxidants ldquo by Sarrami F Yu LJ and Karton A

Journal of computer-aided molecular design 2017 31 905-913

64 Appendix D Online Supplementary Information for ldquo A computational investigation of the

sulphuric acid catalysed 1 4 hydrogen transfer in higher Criegee intermediatesrdquo by

Mackenzie Rae FA and Karton A International Journal of Quantum Chemistry

2018 118 25599

65 Appendix E Online Supplementary Information for ldquo Mechanistic insights into the water-

catalysed ring-opening reaction of vitamin E by means of double-hybrid density

functional theoryrdquo by Sarrami F Kroeger A A and Karton A Chemical

Physics Letters 2018 708 123


92

66 Appendix F Online Supplementary Information for ldquo An assessment of theoretical procedures for

π-conjugation stabilisation energies in enonesrdquo by Yu LJ Sarrami F Karton A

and OrsquoReilly RJ Molecular Physics 2015113 1284-1296

67 Appendix G Online Supplementary Information for ldquo A Reaction barrier heights for

cycloreversion of heterocyclic rings An Achillesrsquo heel for DFT and standard ab

initio proceduresrdquo by Yu LJ Sarrami F OrsquoReilly RJ and Karton Chemical

Physics 2015 458 1-8

68 Appendix H Online Supplementary Information for ldquo Can DFT and ab initio methods describe all

aspects of the potential energy surface of cycloreversion reactions rdquo by Yu LJ

Sarrami F OReilly RJ and Karton A Molecular Physics 2016114 21-33

69 Appendix I Online Supplementary Information for ldquoSol-Gel auto-combustion synthesis and

physicochemical properties of BaAl2O4 nanoparticles electrochemical hydrogen

storage performance and density functional theory ldquoSalehabadi A Salavati-Niasari

M Sarrami F and Karton A Renewable Energy 2017 114 1419-1426

610 Appendix J Online Supplementary Information for ldquo Dy3Al2(AlO4)3 ceramic nanogarnets sol-gel

auto-combustion synthesis characterization and joint experimental and

computational structural analysis for electrochemical hydrogen storage

performancesrdquo by Salehabadi A Sarrami F Salavati-Niasari M Gholami T

Spagnoli D and Karton A Journal of Alloys and Compounds 2018 744 574-582


93

611 Appendix K Online Supplementary Information for ldquo Study of dual encapsulation possibility of

hydrophobic and hydrophilic drugs into a nanocarrier based on bio-polymer coated

graphene oxide using density functional theory molecular dynamics simulation and

experimental methodsrdquo by Moradi S Taran M Mohajeri P Sadrjavadi K

Sarrami F Karton A Journal of Molecular Liquids 2018 262 204-217


94

61 Appendix A Electronic Supplementary Information

Thermochemistry of icosahedral closo-

dicarboranes A composite ab initio quantum-

chemical perspective

Farzaneh Sarrami Li-Juan Yu and Amir Karton

School of Molecular Sciences The University of Western Australia Perth WA 6009 Australia

Supplementary Data


95

Table S1 TAE[(T)] diagnostics for the importance of post-CCSD(T) correlation effects for the species considered in the present study (shown in Fig 1 of the main

text)a

aTAE[(T)] is the percentages of the valence CCSD(T) atomization energy accounted for by the (T) component (for

further details see refs 1 2 3) bTAE[(T)] values are obtained at the CCSD(T)6-31G(d) level of theory cTAE[(T)] values are obtained at the CBS limit from W1-F12 theory dXbull indicates on which B or C atom the radical is centered (see Figure 1)

TAE[(T)]b TAE[(T)]c 6-31G(d) W1-F12

para 15 19 C2B10H12 meta 15 19

ortho 16 20 para 18 22

C2B10H12+ meta 17 21

ortho 18 22 para Bbulld 16 20 para Cbulld 16 20 meta B2bulld 16 20 meta B4bulld 16 R meta B5bulld 16 20

C2B10H12bull meta B9bulld 16 20 meta Cbulld

16 20 ortho B3bulld 16 20 ortho B4bulld 16 R ortho B8bulld 16 20 ortho B9bulld 16 20 ortho Cbulld 17 21


96

Table S2 Deviations and overall error statistics from W1-F12 values of

isomerization ionization CndashH bond dissociation and BndashH bond dissociation energies

for carboranes obtained by standard ab initio methods (kcal molndash1)

QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa

Isomerization meta 021 021 -030 -040

ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555

Error statisticsc RMSD 223 226 1484 1485

MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790

aExtrapolated SCF component used in G4(MP2) theory bBxndashH indicates on which BndashH bond is being broken (see Figure 1) cThe error statistics are over all the chemical properties listed above RMSD = root- mean-square deviation MAD = mean-absolute deviation MSD = mean-signed deviation LD = largest deviation


97

Table S3 Higher-level correction terms E(HLC) used in the G3(MP2) and G4(MP2)

procedures (kcal molndash1)

G3(MP2) G4(MP2)

Isomerization meta 0 0

ortho 0 0

Ionization para 302 -048

meta 302 -048

ortho 302 -048

CndashH BDE para 175 -180

meta 175 -180

ortho 175 -180

BndashH BDE para 175 -180

meta B2ndashHa 175 -180




ortho B3ndashHa 175 -180




aBxndashH indicates on which BndashH bond is being broken (see Figure 1)


98

Table S5 Full References for Molpro 2012 (ref 22) CFOUR (ref 41) and Gaussian 09 (ref 50) (22) MOLPRO version 20121 a package of ab initio programs Werner H-J Knowles P J Manby F R Schuumltz M Celani P Knizia G Korona T Lindh R Mitrushenkov A Rauhut G Adler T B Amos R D Bernhardsson A Berning A Cooper D L Deegan M J O Dobbyn A J Eckert F Goll E Hampel C Hesselmann A Hetzer G Hrenar T Jansen G Koumlppl C Liu Y Lloyd A W Mata R A May A J McNicholas S J Meyer W Mura M E Nicklaszlig A Palmieri P Pfluumlger K Pitzer R Reiher M Shiozaki T Stoll H Stone A J Tarroni R Thorsteinsson T Wang M See also httpwwwmolpronet (41) CFOUR a quantum chemical program package written by JF Stanton J Gauss ME Harding PG Szalay with contributions from AA Auer RJ Bartlett U Benedikt C Berger DE Bernholdt YJ Bomble L Cheng O Christiansen M Heckert O Heun C Huber T-C Jagau D Jonsson J Juseacutelius K Klein WJ Lauderdale F Lipparini DA Matthews T Metzroth LA Muumlck DP ONeill DR Price E Prochnow C Puzzarini K Ruud F Schiffmann W Schwalbach C Simmons S Stopkowicz A Tajti J Vaacutezquez F Wang JD Watts and the integral packages MOLECULE (J Almloumlf and PR Taylor) PROPS (PR Taylor) ABACUS (T Helgaker HJ Aa Jensen P Joslashrgensen and J Olsen) and ECP routines by A V Mitin and C van Wuumlllen For the current version see httpwwwcfourde (50) Gaussian 09 Revision D01 Frisch M J Trucks G W Schlegel H B Scuseria G E Robb M A Cheeseman J R Scalmani G Barone V Mennucci B Petersson G A Nakatsuji H Caricato M Li X Hratchian H P Izmaylov A F Bloino J Zheng G Sonnenberg J L Hada M Ehara M Toyota K Fukuda R Hasegawa J Ishida M Nakajima T Honda Y Kitao O Nakai H Vreven T Montgomery Jr J A Peralta J E Ogliaro F Bearpark M Heyd J J Brothers E Kudin K N Staroverov V N Kobayashi R Normand J Raghavachari K Rendell A Burant J C Iyengar S S Tomasi J Cossi M Rega N Millam N J Klene M Knox J E Cross J B Bakken V Adamo C Jaramillo J Gomperts R Stratmann R E Yazyev O Austin A J Cammi R Pomelli C Ochterski J W Martin R L Morokuma K Zakrzewski V G Voth G A Salvador P Dannenberg J J Dapprich S Daniels A D Farkas Ouml Foresman J B Ortiz J V Cioslowski J Fox D J Gaussian Inc Wallingford CT 2009


99

62 Appendix BElectronic Supplementary Information

Sulphuric acid-catalysed formation of hemiacetal

from glyoxal and ethanol Farzaneh Sarrami Li-Juan Yu Wenchao Wan and Amir Karton

School of Molecular Sciences The University of Western Australia Perth WA 6009

Australia

Supplementary Data


100

Table S1 Reaction profiles (G4(MP2) ΔG298 kJ molndash1) for the uncatalysed reaction of glyoxal and two ethanol molecules and the reactions catalysed by water ethanol formic acid and sulphuric acid

Specie

Catalyst RC1 TS1 INT1 INT2 TS2 INT3 PROD

Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101

Table S3 Full reference for Gaussian 09 (ref 30) (30) Gaussian 09 Revision E01 Frisch M J Trucks G W Schlegel H B Scuseria G E Robb M A Cheeseman J R Scalmani G Barone V MennucciB Petersson G A Nakatsuji H Caricato M Li X Hratchian H P Izmaylov A F Bloino J Zheng G Sonnenberg J L Hada M Ehara M Toyota K Fukuda R Hasegawa J Ishida M Nakajima T Honda Y Kitao O Nakai H Vreven T Montgomery Jr J A Peralta J E Ogliaro F Bearpark M Heyd J J Brothers E Kudin K N Staroverov V N Kobayashi R Normand J Raghavachari K Rendell A Burant J C Iyengar S S Tomasi J Cossi M Rega N Millam N J Klene M Knox J E Cross J B Bakken V Adamo C Jaramillo J Gomperts R Stratmann R E Yazyev O Austin A J Cammi R Pomelli C Ochterski J W Martin R L Morokuma K Zakrzewski V G Voth G A Salvador P Dannenberg J J Dapprich S Daniels A D Farkas Ouml Foresman J B Ortiz J V Cioslowski J Fox D J Gaussian Inc Wallingford CT 2009


102

63 Appendix C Electronic Supplementary Information

Computational design of bio-inspired carnosine-

based HOBr antioxidants



Supplementary Data


103

Figure S1 Atom numbers for the structure carnosine in REAC and INT2 used in

Table 1

Table S1 Atomic polar tensor (APT) charges on the imidazole ring and the halide

atom in the REAC and INT2 (see Figure S1 for atom numbering)

APT charges

REAC

Cl+ INT2

REAC

Br+ INT2

N1 ndash0691 ndash0725 ndash0709 ndash0734

N2 ndash0002 0008 ndash0122 ndash0114

C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919

Imidazole ringa 0019 1011 ndash0111 0882

X ndash0089 0011 0047 0147aSum of the APT charges on the atoms of the imidazole ring


104

Table S2 Bond length of N2ndashX (Aring) (Figure 1) for TS2 in the intramolecular X+

transfer in the N-halogenated derivatives of carnosine shown in Figure 5 (X = Cl and

Br)

Cl+ Br+

Ra N2ndashX (Aring) N2ndashX (Aring)

NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a

p constants are given in parenthesis b

Values taken from reference 37


105

Table S3 Sum of the atomic polar tensor (APT) charges on the N2 (Figure 1) and halide

atoms in TS2 for the intramolecular X+ transfer in the N-halogenated derivatives of

carnosine shown in Figure 5 of the main text (X = Cl and Br)

ap constants are given in parenthesis

Cl+ Br+

Ra N2bullbullbullX+ (au) N2bullbullbullX+ (au)

NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021

OH (ndash037) ndash004 ndash006

NH2 (ndash066) ndash014 ndash016


106

64 Appendix D Electronic Supplementary Information

A computational investigation of sulphuric

acid-catalysed 14-hydrogen transfer in higher

Criegee intermediates

Farzaneh Sarrami FelixA Makenzie-Rae and Amir Karton


Australia

Supplementary Data


107

Figure S1 Optimized transition structures for the uncatalysed water-catalysed and

sulphuric acid-catalysed 14 H-shift reactions in methyl CI


108

Figure S2 Reaction profiles (G4(MP2) ΔG298 kJ molndash1) for the uncatalysed

(black line) water-catalysed (orange line) and sulphuric acid-catalysed (blue line)

reactions for the 14 H-shifts of isoprene CI


109

Figure S3 Reaction profiles (G4(MP2) ΔG298 kJ molndash1) for the uncatalysed (black

line) water-catalysed (orange line) and sulphuric acid-catalysed (blue line) reactions

for the 14 H-shifts of α-pinene CI1


110



for the 14 H-shifts of α-pinene CI2 (CI2-I and CI2-II)


111

Table S2 Full details for reference 59 (Gaussian 09)

[59] MJ Frisch GW Trucks HB Schlegel GE Scuseria MA Robb JR Cheeseman G Scalmani V Barone B Mennucci GA Petersson H Nakatsuji M Caricato X Li HP Hratchian AF Izmaylov J Bloino G Zheng JL Sonnenberg M Hada M Ehara K Toyota R Fukuda J Hasegawa M Ishida T Nakajima Y Honda O Kitao H Nakai T Vreven JA Montgomery Jr JE Peralta F Ogliaro MJ Bearpark J Heyd EN Brothers KN Kudin VNStaroverov R Kobayashi J Normand K Raghavachari AP Rendell JC Burant SS Iyengar J Tomasi M Cossi N Rega NJ Millam M Klene JE Knox JB Cross V Bakken C Adamo J Jaramillo R Gomperts RE Stratmann O Yazyev AJ Austin R Cammi C Pomelli JW Ochterski RL Martin K Morokuma VG Zakrzewski GA Voth P Salvador JJ Dannenberg S Dapprich AD Daniels Ouml Farkas JB Foresman JV Ortiz J Cioslowski DJ Fox Gaussian09 Gaussian Inc Wallingford CT USA 2009


112

65 Appendix E Electronic Supplementary Information

Mechanistic insights into the water-catalysed

ring-opening reaction of vitamin E by means of

double-hybrid density functional theory

Farzaneh Sarrami Asja A Krorger and Amir Karton

School of Molecular Sciences The University of Western Australia Perth WA

6009 Australia

Supplementary Data


113

Figure S1 Reaction profile (∆G298 CPCM(water)-DSD-PBEP86 kJ mol ) for the uncatalysed rearrangement reaction of α-tocopherone to ATQ The bonds being broken and formed in the transition structures are represented by black dashed lines


114

Figure S2 Reaction profile (∆G298 CPCM(water)-DSD-PBEP86 kJ mol ) for the rearrangement reaction of α-tocopherone to ATQ catalysed by one (red line) and two (blue line) water molecules Dashed lines in the transition structures represent bonds being broken and formed whilst in the RCs and PCs dashed lines represent hydrogen bonds


115

Figure S3 Reaction profile (∆G298 CPCM(water)-DSD-PBEP86 kJ molndash1) for the uncatalysed (black line) H2O-catalysed (red line) and 2H2O-catalysed (blue line) rearrangement reaction in the proposed antioxidant candidate 1 (Scheme 1 of the main text) A schematic representation of the TSs is shown in which bonds being broken and formed are represented by dashed lines


116

Figure S4 Reaction profile (∆H298 CPCM(water)-DSD-PBEP86 kJ molndash1)

for the uncatalysed (black line) 1H2O-catalysed (red line) and 2H2O-catalysed

(blue line) rearrangement reaction of candidate 2 to the related quinone


117

Figure S5 Reaction profile (∆H298 CPCM(water)-DSD-PBEP86 kJ molndash1) for the

uncatalysed (black line) 1H2O-catalysed (red line) and 2H2O-catalysed (blue line)

rearrangement reaction of candidate 2 to the related quinone


118

Table S1 Reaction Gibbs free energies (∆G298) calculated at the CPCM(water)-DSD- PBEP86 level for the four possible products (A B C and D) of the radical coupling reaction between the tocopheroxyl radical and HObull (Figure 2 of the main text) ∆G298 values in kJ mol

ndash1are given relative to the free reactants

Intermediate ∆G298

A ndash713 B ndash2317 C ndash2587 D ndash2283


119

66 Appendix F Presentation of the article

Title An assessment of theoretical procedures for π -conjugation stabilisation energies in enones

Authors Yu LJ Sarrami F Karton A

Journal Molecular Physics 113(11) 1284-1296

DOI httpsdxdoiorg 101080002689762014986238 Date of Publication February 2015

120


121

67 Appendix G


Title A Reaction barrier heights for cycloreversion of heterocyclic rings An Achillesrsquo heel for DFT and standard ab initio proceduresrdquo

Authors Yu LJ Sarrami F OrsquoReilly RJ and Karton A

Journal Chemical Physics 2015 458 1-8

DOI httpsdxdoiorg101016jchemphys201507005

Date of Publication September 2015

122


123

68 Appendix H


Title Can DFT and ab initio methods describe all aspects of the potential energy surface of cycloreversion reactions

Author

Yu LJ Sarrami F OrsquoReilly RJ and Karton A

Journal

Renewable Energy 2017 114 1419-1426

DOI httpsdxdoiorg1010800026897620151081418

Date of Publication

September 2015

124


125

69 Appendix I


Title

Sol-Gel auto-combustion synthesis and physicochemical properties of BaAl2O4 nanoparticles electrochemical hydrogen storage performance and density functional theory

AuthorsSalehabadi A Salavati-Niasari M Sarrami F and Karton A

Journal Renewable Energy 2017 114 1419-1426

DOI

httpsdxdoiorg101016jrenene201707119

Date of Publication

December 2017

126


127

610 Appendix J


Title

Dy3Al2(AlO4)3 ceramic nanogarnets sol-gel auto-combustion synthesis characterization and joint experimental and computational structural analysis for electrochemical hydrogen storage performances

AuthorsSalehabadi A Sarrami F Salavati-Niasari M Gholami T Spagnoli D and Karton

Journal Journal of Alloys and Compounds 2018 744 574-582

DOI

httpsdxdoiorg101016jjallcom201802117

Date of Publication

May 2018

128


129

611 Appendix K


Title

Study of dual encapsulation possibility of hydrophobic and hydrophilic drugs into a nanocarrier based on bio-polymer coated graphene oxide using density functional theory molecular dynamics simulation and experimental methods

Authors Moradi S Taran M Mohajeri P Sadrjavadi K Sarrami F Karton

Journal Journal of Molecular Liquids 2018 262 204-217

DOI

httpsdxdoiorg101016jmolliq201804089

Date of Publication

July 2018

130

References

131

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Chem A 2001 105 4446 199 Mauldin Iii R L Berndt T Sipila M Paasonen P Petaja T Kim S Kurten

T Stratmann F Kerminen V M Kulmala M Nature 2012 488 193 200 Boy M Mogensen D Smolander S Zhou L Nieminen T PaasonenP Plass

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Phys 2013 13 3865 201 Percival C J Welz O Eskola A J Savee J D Osborn D L Topping D O

Lowe D Utembe S R Bacak A McFiggans G Cooke M C Xiao P Archibald

A T Jenkin M E Derwent R G Riipinen I Mok D W K Lee E P F Dyke J

M Taatjes C A Shallcross D E Faraday Discuss 2013 165 45 202 L Vereecken D R Glowacki M J Pilling Chem Rev 2015 115 4063 203 M Kumar D H Busch B Subramaniam W H Thompson Phys Chem Chem

Phys 2014 16 22968 204 J M Anglada J Gonzalez M Torrent-Sucarrat Phys Chem Chem Phys 2011 13

13034 205 L Jiang Y S Xu A Z Ding Int J Mol Sci 2013 14 5784 206 L A Curtiss P C Redfern K Raghavachari J Chem Phys 2007 127 124105 207 Goldstein A H Galbally I E Environ Sci Technol 2007 41 1514 208 Volkamer R Jimenez J L San Martini F Dzepina K Zhang Q Salcedo D

Molina L T Worsnop D R Molina M J Geophys Res Lett 2006 33 L17811

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G J Geophys Res 1995 100 9325 211 Grosjean E Grosjean D Fraser M P Cass G R Environ SciTechnol 1996 30

2687 212 Wittrock F Richter A Oetjen H Burrows J P Kanakidou M

Myriokefalitakis S Volkamer R Beirle S Platt U Wagner T Geophys Res Lett

2006 33 L16804 213 Ervens B and Volkamer R Atmos Chem Phys 2010 10(17) 8219 214 Silva GD Phys Chem Chem Phys 2010 12(25) 6698 215 Silva GD The Journal of Physical Chemistry A 2010 115(3) 291 216 Silva GD Graham C and Wang ZF 2009 Environ Science amp tech 44(1) 250 217 Volkamer R San Martini F Molina LT Salcedo D Jimenez JL Molina

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J Geophys Res Atmos 2008 113 D15303 219 Zhang Q Jimenez JL Canagaratna MR Allan JD Coe H I Ulbrich

MRAlfarra Takami A Middlebrook AM Sun YL Geophys Res Lett 2007 34

L13801 220 Hazra MK Francisco JS Sinha A J Phys Chem A 2007 118 4095 221 Liggio J Li SM McLaren R Environ Sci Tech 2005 39 1532 222 Gomez ME Lin Y Guo S Zhang R J Phys Chem A 2014 119 4457 223 Hastings WP Koehler CA Bailey EL De Haan DO Environ Sci Tech

2005 39 8728 224 Haan DOD Corrigan AL Smith KW Stroik DR Turley JJ Lee FE

Tolbert MA Jimenez JL Cordova KE Ferrell GR Environ Sci Tech 2009 43

818225 Corrigan AL Hanley SW De Haan DO Environ Sci Tech 2008 42 4428 226 Gomez ME Lin Y Guo S Zhang R J Phys Chem A 2014 119 4457 227 Jang M Kamens RM Environ Sci Tech 2001 35 4758

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metal bonds 1995 10 234 Siebert W International Meeting on Boron Chemistry Royal Society of Chemistry

Information Services 1997 235 King R Bruce Chem Rev 2001 101 1119 236 Štiacutebr B Chem Rev 1992 92 225 237 Saxena A K Hosmane N S Chem Rev 1993 93 1081 238 Sivaev I B Bregadze V I Sjoberg S Chem Commun 2002 67 679 239 Deng L Xie Z W Chem Rev 2007 251 2452 240 Grimes R N Academic Press 2011 241 Olid D Nuntildeez R Vintildeas C Teixidor F Chem Soc Rev 2013 42 3318 242 Plešek J Chem Rev 1992 92 269 243 Farra s P Juaacuterez-Peacuterez E J Lepšik M Luque R Nuacutentildeez R Teixidor F Chem

Soc Rev 2012 41 3445 244 In Boron Science New Technologies and Applications Hosmane N S Ed CRC

Press Boca Raton FL 2011 245 Reed C A Chem Commun 2005 1669 246 Heying TL Ager JW SL Clark Jr Mangold DJ Goldstein HL Hillman

M Polak RJ Szymanski JW Inorg Chem 1963 2 1089 247 Fein MM Bobinski J N Mayes N Schwartz MS Cohen Inorg Chem 1963 2

111 248Hoffmann R Lipscomb WN Inorg Chem 1963 2 231 249 Kaesz HD Bau R Beall HA Lipscomb WN J Am Chem Soc 1967 89

4218 250 Kaczmarczyk A Dobrott RD Lipscomb WN Proc Natl Acad Sci 1962 48

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62

321 A computational investigation of the sulphuric acid catalysed 14-hydrogen transfer in higher Criegee intermediates


TitleA computational investigation of the sulphuric acid catalysed 14-hydrogen transfer in higher Criegee intermediates

Authors Sarrami F Mackenzie Rae FA and Karton A

Journal International Journal of Quantum Chemistry 2018 118 e25599

DOI httpsdxdoiorg 101002qua25599 Date of Publication February 2018

Graphical TOC

63

58

59

60

61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


63

58

59

60

61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


58

59

60

61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


59

60

61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


60

61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


61

62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


62

63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


63

64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


64

65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


65


66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



66







Graphical TOC

67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


67

68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


68

69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


69

70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


70

71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


71

72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


72

73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


73

74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


74


75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



75








C2B10H12







polymers and others


76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



76


closo-dicarboranes







hexacoordinate















77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



77























78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



78







79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


79

80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


80

82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


82

83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


83

84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


84

85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


85

86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


86


87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



87













provided















88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



88


































89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



89


































90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



90














6X)















91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



91














2018 118 25599






92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



92







Physics 2015 458 1-8














93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



93







94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



94







Supplementary Data


95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



95


text)a




para 15 19 C2B10H12 meta 15 19


C2B10H12+ meta 17 21





96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



96




QCISD(T)

CCSD(T) SCF SCF

6-31G(d) 6-31G(d) 6-31G(d) VTQZa


ortho 064 065 183 163

Ionization para -488 -445 -1748 -1484

meta -548 -577 -1938 -1790

ortho -522 -547 -1446 -1748

CndashH BDE para 020 032 -1602 -1590

meta 005 019 -1584 -1566

ortho 007 023 -1506 -1493

BndashH BDE para -058 -058 -1539 -1560

meta B2ndashHb -071 -071 -1541 -1555

meta B4ndashHb -064 -064 -1539 -1560

meta B5ndashHb -053 -053 -1535 -1561

meta B9ndashHb -056 -054 -1532 -1556

ortho B3ndashHb -072 -072 -1542 -1562

ortho B4ndashHb -060 -058 -1521 -1542

ortho B8ndashHb -054 -052 -1524 -1550

ortho B9ndashHb -048 -047 -1526 -1555


MAD 130 133 1402 1404

MSD -116 -114 -1380 -1385

LD -548 -577 -1938 -1790



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



97



G3(MP2) G4(MP2)


ortho 0 0


meta 302 -048

ortho 302 -048


meta 175 -180

ortho 175 -180












98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



98



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



99





Australia

Supplementary Data


100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



100


Specie


Uncatalysed 157 1726 -117 23 1591 NA -203

Water 455 1482 102 364 1273 56 -203

Ethanol 400 1350 89 165 1148 07 -203

Formic acid 74 574 -180 151 598 -140 -203

Sulphuric acid 86 386 -171 179 312 -173 -203


101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



101



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



102






Supplementary Data


103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



103


Table 1



APT charges

REAC

Cl+ INT2

REAC

Br+ INT2



C1 0291 0282 0300 0285

C2 0015 ndash0032 0017 ndash0035

C3 0135 0188 0135 0191

H1 0123 0204 0119 0198

H2 0150 0181 0148 0173

H3 Nil 0904 Nil 0919




104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



104



Br)

Cl+ Br+


NO2 (078) 1764 1875

CHO (042) 1782 1890

H (00) 1790b 1893

OH (ndash037) 1804 1896

NH2 (ndash066) 1816 1900 a




105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



105





Cl+ Br+


NO2 (078) +065 +063

CHO (042) +059 +055

H (00) +023 +021




106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



106







Australia

Supplementary Data


107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



107




108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



108





109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



109





110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



110





111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



111




112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



112







6009 Australia

Supplementary Data


113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



113



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



114



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



115



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



116





117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



117





118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



118






119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



119






120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

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2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


120


121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



121

67 Appendix G







122


123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

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127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


122


123

68 Appendix H



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Journal



Date of Publication

September 2015

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69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


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May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









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2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



123

68 Appendix H



Author


Journal



Date of Publication

September 2015

124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

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129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








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133











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134







References

135


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Phys 1989 90 5622

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2018 71 238

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137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


124


125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

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134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



125

69 Appendix I


Title




DOI


Date of Publication

December 2017

126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










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132








References

133











2007 3(2) 407

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134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


126


127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



127

610 Appendix J


Title




DOI


Date of Publication

May 2018

128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


128


129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143



129

611 Appendix K


Title




DOI


Date of Publication

July 2018

130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

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143


130

References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

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136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


References

131










References

132








References

133











2007 3(2) 407

References

134







References

135


Phys









Phys 1989 90 5622

References

136















2018 71 238

References

137












2009 11 2899

References

138











References

139












1596

References

140
















References

141














References

142









729

References

143


References

132








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Documents

Chapter 3: Atmosphere chemistry application · Chapter 3: Atmosphere chemistry application 66 3.2.2 Sulphuric acid-catalysed formation of hemiacetal from glyoxal and ethanol Presentation