Synthesis and Spectral Properties of Some bis-Subtituted Formazans

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  • Synthesis and Spectral Properties of Some bis-Subtituted FormazansSubmitted To: Dr. Khurram Shahzad MunawarSubmitted By: Shakeel Ahmad Khan (14003140007)

    Program: MS (Chemistry) 3rdDepartment of Chemistry, University of Management and Technology LahoreH. Tezcan / Spectrochimica Acta Part A 69 (2008) 971979**2

  • Introduction about FormazansImportance of workAim of the StudResearch Methodologya. Chemicals Used b. Formation outline for Formazansc. Scheme for the Synthesis of Formazansd. Instrument UsedResult and Discussiona. Elemental Analysisb. Spectral Analysis (1HNMR 400MHz, Mass Spectrometer, UV-Visible Spectrometer, FTIR).Conclusion and Future AspectsReferences

    List of Contents*

  • Formazans:Formazans and their derived Metal complexes are colored. They impart color due to -* transitions of electrons in formazan skeleton (-N=NC=NNH-). [1]

    a. TPF b. p-SCSPF Introduction

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  • Formazans:Formazans dyes are ranging from Red to Orange as well as Blue color. Its color Depending upon the structure [2, 3].

    Color Range For Formazan DyesFormazans are Polydentate Ligands with donor atoms [4,5].

    Introduction*

  • Formazans:Formazans dyes have more light fastness, wash fastness, bleach fastness, and rub fastness.These properties make them Unique for Industrial dyes sector as compared to other dyes such as Acid dyes, Mordant dyes, etc.[2, 3].

    Wash fastness Light Fastness of dyes

    Importance of work*

  • Objective of this study involve to synthesize Water soluble macromolecule bis-formazans with various structures [2].

    Objective of this study also involve to investigate their spectral properties [2].

    Aim of this Study1H NMR Spectra IR Spectra Mass Spectra UV-vis Spectra *

  • Following Chemicals (Sigma Aldrich) are used in this study

    Anthranilic acid Benzaldehyde O-OH Benzaldehyde

    m-OH Benzaldehyde p-OH Benzaldehyde p-PDSAResearch Methodology*

  • Following Chemicals (Sigma Aldrich) are used in this study

    CH3OH DMSO NaNO2

    HCl Sodium acetate CDCl3

    Research Methodology*

  • Formation outline for Formazans [6]. a. b. c.

    d. e. F.

    Research MethodologyDiazotizationHydrazine HydrazonesDiazotizationCoupling ReactionFormazan Dyes*

  • Research MethodologyScheme for the Synthesis of Formazans [2]. *

  • Research MethodologyScheme for the Synthesis of Formazans [2].

    The structure of the formazans synthesized

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  • Following Instruments are used in Study [2].a. 1HNMR (400MHz) c. Mass Spectrometer

    b. UV-visible SpectrophotometerResearch Methodology*

  • Following Instruments are used in Study [2].d. Elemental analyzer. e. FTIR

    Research Methodology

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    Result and Discussion*

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  • Table 2. The 1H NMR data of formazans (15) (400 MHz, in CDCl3).Result and Discussion*

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  • Figure 1. 1H NMR spectra of CSPF, o-HCSPF, p-HCSPF measured in CDCl3 at 25C.Result and Discussion

    Ar-H (8.50-6.90 m, 21H)Ar-H (7.92-6.85 m, 19H)Ar-H (7.98-6.65 m, 19H)N-H (2.05-1.70 s, 2H)N-H (2.75-2.60 s, 2H)N-H (2.50-2.25 s, 2H)Ar-OH (3.20 s, 2H)Ar-OH (3.10 s, 2H)SO3H (11.28 s, 1H), COOH (10.90 s, 2H)SO3H (11.27 s, 1H), COOH (10.80 s, 2H)SO3H (10.85 s, 1H), COOH (10.85 s, 2H)*

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  • Table 3. IR spectral data of formazans (15) (in KBr, cm1)Result and Discussion*

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  • Fig. 2. IR spectra of: (A) TPF; (B) CSPF; (C) o-HCSPF; (D) m-HCSPF; (E) p-HCSPF.

    Result and Discussion*18

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  • Fig. 3. Mass spectrum of the formazan (p-HCSPF, 5).Result and Discussion*

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  • Scheme 4. Proposed fragmentation pattern of p-HCSPF (5). Result and Discussion*

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  • Table 4UVvis absorption max values of formazans (15) (CH3OH, 104 mol l1)Result and DiscussionFig. 4. The electronic absorption of formazans in CH3OH, 104 mol/l.*

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  • Fig. 5. The electronic absorption in CH3OH, DMSO, DMF, 1,4-Dioxane, CH2Cl2104 mol/l: (A) compound 1; (B) 2; (C) 3; (D) 5.Result and Discussion*

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  • From the present study it is evident that the lowest yield was obtained by the o-hydroxy carboxy sulfo phenyl formazans (o-HCSPF) in 25 formazans.The relative increase in yield obtained with both m-hydroxy carboxy sulfo phenyl formazans (m-HCSPF)and p-hydroxy carboxy sulfo phenyl formazans (p-HCSPF). Future AspectsTo evaluation and characterization of synthesized formazans in medical applications. Conclusion*

  • 1. H. Tezcan / Spectrochimica Acta, Part A 70 (2008) 9739822. H. Tezcan / Spectrochimica Acta, Part A 69 (2008) 9719793. A.M. Mattson, C.O. Jensen, R.A. Dutcher, J. Am. Chem. Soc. 70 (1948) 1284.4. G. Arnold, V.C. Schiele, Spectrochim. Acta 25 (1966) 685. 5. G.M. Abou-Elenien, J. Electroanal. Chem. 375 (1994) 301.6. H. Tezcan, S. Can, R. Tezcan, Dyes Pigments 52 (2002) 121. References*

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