i

VOLUME 29 ISSUE 4 2019 MENCEX (4) 361 –478 (2019)

Mendeleev CommunicationsCONTENTS

MOF-based sensors

Gases

LiquidsToxic

compounds

Explosives

MOF

361 Metal-organic frameworks as materials for applications in sensors

Leonid M. Kustov, Vera I. Isaeva, Jan Prech, Kamal Kumar Bisht

N

NNAr

RN

NN

NN

R

Ar

Domino transformations

369 A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne

Sravya Gundala, Mallikarjuna Reddy Guda, Albert F. Khasanov, Dmitry S. Kopchuk, Alexey P. Krinochkin, Sougata Santra, Grigory V. Zyryanov, Padmavathi Venkatapuram, Jarem Raul Garcia, Valery N. Charushin

SO2Et

CO2Me

O

CO2Me

O

chemically

in vivo

372 Simple antitumor model compounds for cross-conjugated cyclopentenone prostaglandins

Nikolay S. Vostrikov, Leonid V. Spirikhin, Alexander N. Lobov, Airat M. Gimazetdinov, Zulfiya R. Zileeva, Yulia V. Vakhitova, Zainutdin R. Macaev, Kasimir K. Pivnitsky, Mansur S. Miftakhov

OR1R2

O O

N

NH

O

Ts

R2R1

O

O

N

CHO

CHO

TsNH4OAc

C(4)

C(3) C(24)

C(2)C(1)

C(39)

C(38)

C(42)

C(43)

O(23)

N(25)

N(11)

S(1)

O(14)

O(1)O(2)

O(8)

C(40)

C(41)

C(5)

C(6)

C(7)

C(12)C(9)C(10)

C(30)

C(26)

C(25)

C(27)

C(28)

C(31)

C(29)

C(13)

C(16)

C(17)C(15)

C(20)

C(23)

C(21) C(22)

C(18)

C(19)C(37)

C(36)

C(35)

C(34)

C(33)

C(32)

375 Synthesis and cytotoxicity of novel gggg-piperidone-containing dibenzo-1,7-diaza-14-crown-4 ethers

Anh T. Le, Van T. T. Tran, Hieu H. Truong, Linh M. Nguyen, Duc M. Luong, Thuyen T. Do, Dat T. Nguyen, Nhung T. Dao, Dat T. Le, Anatoly T. Soldatenkov, Victor N. Khrustalev

Ar1–I Ar2(Alk)+

CuI/3-Pphen(5 mol%)

Ar2(Alk)Ar1

85–99%

NNP(O)(OEt)2

3-Pphen

H2O100 °C,3–6 h

378 Enhanced catalytic activity of CuI /diethoxy-phosphoryl-1,10-phenanthrolines in ‘on water’ Cu-catalyzed Sonogashira reaction

Alexander Yu. Mitrofanov, Irina P. Beletskaya

380 Simple H2-free hydrogenation of unsaturated monoterpenoids catalyzed by Raney nickel

Alexey A. Philippov, Andrey M. Chibiryaev, Oleg N. Martyanov

FOCUS ARTICLE

COMMUNICATIONS

ii

85 atm1 atm

CO CO

CxHy

Catalyst: FeK/Sibunit or FeCuK/Sibunit

CO2 + H2

382 CO2 hydrogenation on Fe-based catalysts doped with potassium in gas phase and under supercritical conditions

Yana A. Pokusaeva, Aleksey E. Koklin, Valery V. Lunin, Victor I. Bogdan

NC

CNPh

CNNC

Ph

N

S

S

CNNC

Ph

N

S

CN

CN

Ph

NCCN

Ph

CN

NCPh

N

S

S

S

Linear or branched topology for organic solar cells?

22

2 2

2

2

385 Effect of branching on the physical and photovoltaic properties of donor–acceptor oligomers based on triphenylamine

Alexander N. Solodukhin, Yuriy N. Luponosov, Artur L. Mannanov, Petr V. Dmitryakov, Svetlana M. Peregudova, Sergey N. Chvalun, Dmitry Yu. Parashchuk, Sergey A. Ponomarenko

OHHO

OH

OH

OHHO

HO

HO

X X

XX

OPO

O SMe

Me

OO

OO

X

NN

N NN

N

NN

N

NN

N

NN

NNN

N

NN

N

NN

N

R2 R2

R2

R2

R2R2

R2

R2

O

OO

O

X X

X

X =

R1

R1

R1

R1 R1

R1

R1

R1

R1 = H, Me

2 steps

R2 = PhCH2,(anthracen-9-yl)methyl

388 Click reaction in the synthesis of novel thiophosphorylated ligands for electrochemical hydrogen evolution

Irina R. Knyazeva, Victoria I. Matveeva, Vera V. Khrizanforova, Victor V. Syakaev, Yulia H. Budnikova, Wolf D. Habicher, Alexander R. Burilov

R1

R2

CN

CN +X

X

R1

NC

NC X

X

R2

X = CN, 6 examples, 48–72%X = COOMe, 6 examples, 38–67%

graphite anodeFe cathode

constant current electrolysisundivided cell

PyHBr (0.75 equiv.) / MeCN

391 Pyridinium bromide as a new mediator for electrochemical transformations involving CH-acids

Anatoly N. Vereshchagin, Evgeniya O. Dorofeeva, Michail N. Elinson, Victor A. Korolev, Mikhail P. Egorov

(CH2)n

ZnBr

COOMe

N

MeO

MeO

(CH2)n

O

N

MeO

MeO

O

O

+

or

for n = 2–4 for n = 1

N

MeO

MeO

393 Reaction of methyl bromocycloalkanecarboxylates with zinc and dihydroisoquinoline derivative

Elena A. Nikiforova, Nikolay F. Kirillov, Vladislav S. Melekhin, Pavel A. Slepukhin

395 Skeleton pseudomorphs of nanostructured silver for the surface-enhanced Raman spectroscopy

Anna A. Semenova, Sergey V. Savilov, Alexander E. Baranchikov, Vladimir K. Ivanov, Eugene A. Goodilin

PbS: Eg = 0.46 eV

~Pb0.92Ag0.08S: Eg = 0.51 eV

~Pb0.88Ag0.12S: Eg = 0.54 eV

Ag2S: Eg = 0.89 eV

0.4

0.3

0.2

0.1

0.00.4 0.6 0.8 1.0 1.2 1.4 1.6

h– w/eV

[h–w

* F(R

∞)]

2/e

V2

[001]

[100][010]

Ehkl

398 Thermal, elastic and optical properties of nanostructured Pb1–xAgxS solid solutions

Stanislav I. Sadovnikov

iii

I–

I3–

Counter electrode

CuNi0.25@C

Ni@C

Cu@C

400 Synthesis of MOF-derived bimetallic nanocarbons CuNi@C with potential applications as counter electrodes in solar cells

Lizbeth Marroquín Tijerina, Cesar M. Oliva González, Boris I. Kharisov, Thelma E. Serrano Quezada, Yolanda Peña Méndez, Oxana V. Kharissova, Idalia Gómez de la Fuente

–1.2

–1.4

–1.8

–2.0

–1.6

0 5 10 15 20

lg (

s/S

cm–1

)

Dopant content (wt%)

SiO2

SiO2–PO3H2

SiO2–SO3H

SiO2N

N

NH

O

HO

OH

OP

N

NN

O

nO

PhEPBI

403 Effect of the nature of functional groups grafted on the surface of silica nanoparticles on properties of the hybrid proton-conductive membranes based on N-phosphorylated polybenzimidazole

Anna A. Lysova, Igor I. Ponomarev, Andrei B. Yaroslavtsev

MicrocrystalTiOy

25 µm

High-energy ball-milling

Nanocrystal TiOy

30 nm

Annealing

Orderedmonoclinic Ti5O5

[C/2m (A/2m)]

Ordered orthorhombic Ti(2+d1)O(2+d2)

(Immm)

405 Disorder–order phase transition in nanocrystalline titanium monoxide with two-sublattice ordering of structural vacancies

Maxim G. Kostenko, Albina A. Valeeva

p21212

p421m408 Chemically induced symmetry breaking

in the crystal structure of guanidinium uranyl sulfate

Vladislav V. Gurzhiy, Olga S. Tyumentseva, Elena V. Belova, Sergey V. Krivovichev

C(1) C(2)

C(3)

C(4)

C(5)

C(6)

O(1)

O(2)

C(7)

O(3)

C(8)

N(1)

0 1 2 3 4 5 6 7 8r /Å

F(r

)

O(2

)···N

(1)

O(1

)···N

(1)

411 Molecular structure of noradrenaline according to gas-phase electron diffraction data and quantum chemical calculations

Ekaterina P. Altova, Anatolii N. Rykov, Maxim A. Abaev, Ilya I. Marochkin, Anna L. Vilkova, Mikhail V. Popik, Igor F. Shishkov

N

N

Me

Me

O

NH

O

+ ROO

kinhib = 2.5 × 106 dm3 mol–1 s–1

f = 2.0

ROOH

H

H

414 6-Amino-5-hydroxy-2,3-dimethylpyrimidin-4(3H)-one as an efficient inhibitor of free radical oxidation

Stanislav A. Grabovskiy, Yulia S. Grabovskaya, Arcadiy V. Antipin, Natalia N. Kabal’nova

Ph CO2MeCO2Me

D–A spiropentane

EtAlCl2

Nu Nu

CO2Me

CO2MePh

Ph

CO2Me

CO2Me+NN

CO2Me

Me

NN

CO2MeMeCl

=Nu

~ 6 : 1

EtAlCl2

Cl

PhCO2Me

CO2Me

417 4-Phenylspiro[2.2]pentane-1,1-dicarboxylate: synthesis and reactions with EtAlCl2 and 4,5-diazaspiro[2.4]hept-4-ene derivative

Dmitry A. Denisov, Denis D. Borisov, Konstantin V. Potapov, Roman A. Novikov, Yury V. Tomilov

iv

N O

ClR

O=N–OSO3H

+

R Cl

Cl

NO

N O

Cl

R

Cl R

R = Ar

R = Alk

14 examples51–95% yield

419 Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichloro- cyclopropanes

Oksana B. Bondarenko, Zaur M. Garaev, Arseniy I. Komarov, Lyubov I. Kuznetsova, Svetlana V. Gutorova, Dmitry A. Skvortsov, Nikolai V. Zyk

Si Si

Si Si

O

OO

O

Ph Ph

PhPh

O

O

HO

HO

H

Hn

Si Si

Si Si

O

OO

O

Ph Ph

PhPh

OH

OH

HO

HO

NH3

100 °C,4 h

421 Condensation of all-cis-tetraphenylcyclotetrasiloxane-tetraol in ammonia: new method for preparation of ladder-like polyphenylsilsesquioxanes

Anton A. Anisimov, Natalia V. Polshchikova, Yuliya S. Vysochinskaya, Pavel A. Zader, Galina G. Nikiforova, Alexander S. Peregudov, Mikhail I. Buzin, Olga I. Shchegolikhina, Aziz M. Muzafarov

0.8

0.6

0.4

0.2

0.01.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8

VR/V0

Arb

itrar

y un

its

HD1

HD1

HD1

HD1(GL–HD1)2 GL2–HD1

424 Quantitative characterization of oligomeric state of G-quadruplex antithrombin aptamers by size exclusion HPLC

Rugiya R. Alieva, Elena G. Zavyalova, Vadim N. Tashlitsky, Alexey M. Kopylov

X

Quenching of fulvic acid fluorescencedue to complexation with tricyclic antidepressants (TAs)

1.0

0.8

0.6

0.4

0.2

0.00 2 4 6 8 10

[TA]0 /10–4 mol dm–3

F/F

0

Imipramine: X = NCH2CH2CH2NMe2

Desipramine: X = NCH2CH2CH2NHMe

Amitriptyline: X = C=CHCH2CH2NMe2

Nortriptyline: X = C=CHCH2CH2NHMe

426 Intermolecular interactions between natural humic substances and tricyclic antidepressants

Ekaterina D. Mordvinova, Marina V. Parkhats, Yong Chen, Ivan P. Pozdnyakov

N

N N

Me

NO2

NO2

Me N

N N

Me

NO2

Nu

Me

44–98%

Nu–

Nu– = –NRR', –OR, –SR

429 A new general synthesis of functionally substituted pyrazolo[1,5-a]pyrimidines

Tatyana K. Shkineva, Irina A. Vatsadze, Igor L. Dalinger

O O

Ph

OEtPh

R

ClO4

N N

Ph

Ph

R

AcONH4

N O

Ph

HPh

R

ClO4

R'X

R' NH2

X = OEt for R' = AlkX = NHR' for R' = Ar

432 Reactions of 1H-pyrano[3,4-c]pyran-7-ium perchlorates with ammonium acetate and amines: synthesis of 2,7-naphthyridines and pyrano[3,4-c]-pyridinium salts

Konstantin F. Suzdalev, Alina V. Krachkovskaya, Gennadii S. Borodkin, Pavel A. Galenko-Yaroshevsky, Arnold V. Tikhonov, Sergey V. Kurbatov

ArnPh3–nPH CF3CO2

OH

OH

PArnPh3–n

O

OCF3CO2

Ar = 4-MeOC6H4 n = 1, 2, 3

O

O

PArnPh3–n

CF3CO2

Br2 Br2

92–95%

90–95%

435 Versatile approach to naphthoquinone phosphonium salts and evaluation of their biological activity

Nadezhda R. Khasiyatullina, Vladimir F. Mironov, Sumbel K. Gumerova, Alexandra D. Voloshina, Anastasia S. Sapunova

v

NH2

NH3 X–2 RX

NH3 X–

3 RX

CO2

+

DMFor

DMA

– HX

H2NX– HR2N

X–R3N

438 Selective Hofmann alkylation of aromatic-aliphatic diamines in the presence of carbon dioxide

Alexei G. Balybin, Yuri M. Panov, Ludmila V. Erkhova, Dmitry A. Lemenovskii, Dmitry P. Krut’ko

Cl–

Prospidium chloride

N

N

N

N

OH

Cl

OH

ClCl–

441 Solvation and ion–ion interactions in aqueous and non-aqueous solutions of cationic cytostatic agent prospidium chloride

Andrey V. Kustov, Tatiyana V. Kudayarova, Olga A. Antonova, Nataliya L. Smirnova, Andrey A. Kladiev, Arseniy A. Kladiev

N

HN

S N

N

HN

S N N

NH

SN

Cu Cu

Cl

Cl

Cl

ClCuCl2

EtOH

Two Cu2+ reduction peaks at 0.25–0.50 V

444 Binuclear copper(ii) complex with 2-imidazolyl-benzothiazole and bridged chloride ligands

Elena S. Barskaya, Artem V. Rzheutskiy, Anna A. Moiseeva, Victor A. Tafeenko, Nikolay V. Zyk, Elena K. Beloglazkina

Ba Ba

Ba

BaBa

Ba NiO

O

447 Magnetic properties of a linear dioxonickelate(ii) ion imbedded in apatite-type strontium and barium phosphates

Pavel E. Kazin, Mikhail A. Zykin, Lev A. Trusov, Alexander V. Vasiliev

~7 nm[100]

[010]

single dyemolecules

2D crystal with1D substructure

π-stacked intermediates

450 One-dimensional substructure of cyanine dye J-aggregate monolayers resulting from non-classical multistage crystallization

Valery V. Prokhorov, Sergey I. Pozin, Olga M. Perelygina, Eugene I. Mal’tsev

HCNCu

452 Noncovalent bonding of copper atoms to the nitrogen-containing sites of hydrogenated diamond surfaces

Vladimir Yu. Osipov, Danil W. Boukhvalov, Kazuyuki Takai

C2H6 + O2

C2H4 + H2O

1 atm360 °C

100 atm280 °C

MoVNbTeOx MoVNbTeOx

Te4+ ® Te0

irreversible catalystdeactivation

stable catalytic activity for over 40 h

455 Advantages of ethane oxidative dehydrogenation on the MoVNbTeOx catalyst under elevated pressure

Igor I. Mishanin, Viktor I. Bogdan

vi

Si

Si

O

Ar

PR2

MeMe

MeMe

SiSiO

Me

Me Me

Me

Pt P

R

R Si

Si

O

MeMe

MeMe

Pt

Karstedt’s catalyst

Pt

Si

Si

O

MeMe

MeMe Ar

R = But, CyAr = Ph, 2,6-(MeO)2C6H3, 2-Me2NC6H4, 2,4,6-Pr3C6H2

i

458 Effect of Buchwald-type ligands on platinum catalyzed hydrosilylation of vinyl terminated polydimethylsiloxane

Ruslan Yu. Lukin, Dmitry A. Emelyanov, Aleksander D. Kachmarzhik, Aleksander V. Sukhov, Oleg G. Sinyashin, Dmitry G. Yakhvarov

SiO

SiMe

Me

Me Me

O

O

O

nO

461 Synthesis of siloxane analogue of polyethylene terephthalate

Anton A. Anisimov, Elena A. Kuvandykova, Alexander I. Buzin, Aziz M. Muzafarov

HetAr

L

M, M*

PR4S

R3

PR2 S

R1

L is

M is Eu3+, Am3+

Aqueous phase

Organic phase

HetAr is bipy, pyR1, R2, R3, R4 are alkyl, aryl

Shaking MLn

M*

463 N,S-containing soft ligands for extractive separation of f-metals: synthesis and unexpected inverse selectivity

Gladis G. Zakirova, Petr I. Matveev, Dmitrii Yu. Mladentsev, Mariia V. Evsiunina, Viktor A. Tafeenko, Nataliya E. Borisova

CoCl2

NiCl2

CuCl2

MeOH

MeCN

MeSH

MeSH

MeSH

MeOH

MeCN

MeNO2

MeCN

MeNO2

MeOH

MeNO2

Tube filled with CoCl2, NiCl2 or CuCl2 on a support

Retention volumes from air

air air

>

>

>

>

>

>

>

>

>

466 Sorbents based on transition metal salts for the retention of low molecular weight N-, O- and S-containing organic compounds from the air flow

Oleg V. Rodinkov, Galina A. Zhuravleva, Andrey Yu. Vlasov

0.8

0.6

0.4

0.2

0.0

P/M

Pa

R (

arbi

trar

y un

its)600

400

200

00 1 2 3 4 5

t/s

1 2 3

4 5 6

469 Ignition of hydrogen–methane–air mixtures over Pd foil at atmospheric pressure

Nikolai M. Rubtsov, Victor I. Chernysh, Georgii I. Tsvetkov, Kirill Ya. Troshin, Igor O. Shamshin

40

30

10–4 10–3 10–2 10–1

cNaCl/M

T/°

C

Phase separation temperatures

Cl– per one star one arm one monomer

472 The behavior of thermoresponsive star-shaped poly-2-isopropyl-2-oxazoline in saline media

Alina I. Amirova, Alexey N. Blokhin, Alla B. Razina, Andrey V. Tenkovtsev, Alexander P. Filippov

475 Notice to Authors 2019