12311

11277

كارشناسي ارشد

شيمي آلي

اصفهان: دانشگاه صنعتي اصفهان، دانشكده شيمي

1395

پانزده، 121ص.: مصور، جدول، نمودار

ص. ع. به فارسي و انگليسي

عبدالحسين دباغ

مهران غياثي، عليرضا نجفي چرمهيني

1396/01/15

كتابنامه

شيمي

شيمي

ID11277

Synthesize of New Derivatives of Salicylic Acid from 1 3 5 Trimethyl benzene and 1 3 5 Trihydroxy benzene and Theoritical Study of Intramolecular Interactions Nature of 2 4 6 Trihydroxy benzene 1 3 5 Tricarboxylic Acid Elham Ghaderi e ghaderi@ch iut ac ir Date of Submission 2017 02 13 Department of Chemistry Isfahan University of Technology Isfahan 84156 8311 IranDegree M Sc Language FarsiSupervisor H A Dabbagh Prof dabbagh@cc iut ac ir AbstractIn this project 5 methyl 4 6 dinitroisophthalic acid was synthesized from oxidation of 2 4 dinitro 1 3 5 trimethyl benzene The compounds acetic acid 3 5 diacetoxy 2 4 dimethyl phenyl ester 2 4 6 triacetoxy benzoic acid methyl ester 2 4 diacetoxy 6 hydroxy benzoicacid methyl ester 6 acetoxy 3 acetyl 2 4 dihydroxy benzoic acid metyl ester 4 acetoxy 3 acetyl 2 6 dihydroxy benzoic acid metyl ester 3 5 diacetyl 2 4 6 trihydroxy benzoic acidmetyl ester were synthesized from the Friedel Crafts acylation reaction of electron rich arene acetic acid 3 5 diacetoxy phenyl ester using chloroformate acylating reagent The syntesizedcompounds were characterized by GC Mass 1H NMR 13C NMR and FT IR Fries rearrangmentreaction of acetic acid 3 5 diacetoxy phenyl ester was used for the synthesis of derivatives salicylates In second part of this project theoretical studies on four pasibble tautomer of 2 4 6 trihydroxy benzene 1 3 5 tricarboxylic acids using quantum chemistry calculations areperformed Tautemric structure and all relevant conformer were optimized by MP2calculation at the 6 311 G d p basis set The total energy relative energy and optimizedgeometries were calculated Energy data showed that enolic form of 2 4 6 trihydroxy benzene 1 3 5 tricarboxylic acid to be most stable structure among all conformers In thefollowing Stable conformer of each class determined and factors affecting on stability thisconformers examined and formation cooperative hydrogen bonds in these structures wasrecognized as a stability factor Finally natural band orbital NBO theory and atoms inmolecule AIM analysis are applied to assess the nature of the hydrogen bonds in stableconformer each category and to account their effects on the stability of the moleculararrangement The data obtained by the analysis of the AIM and NBO demonstrate toformation of strong hydrogen bonding as a factor in the stability of conformer each category Keywords Friedel Crafts acylation Fries rearrangment hydrogen bond natural band orbital atoms in molecule

عبدالحسين دباغ

مهران غياثي، عليرضا نجفي چرمهيني