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Gallic acid-cholesterol conjugate synthesis, spectroscopic characterization and quantum chemical calculations: Experimental and theoretical approach

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Title Gallic acid-cholesterol conjugate synthesis, spectroscopic characterization and quantum chemical calculations: Experimental and theoretical approach
 
Creator Ansari, Nadeem Ahmad
Srivastava, Sangeeta
Aleem, Sadaf
 
Subject Steglich esterification
HOMO-LUMO
MEP
AIM
NLO
 
Description 1309-1315
Gallic acid is the major constituent in fruits Phyllanthusemblica (amla), of the family phyllanthaceae. Gallic acid was
first methylated to 3,4,5 trimethoxygallic acid, which upon esterification using steglich method with cholesterol resulted in
the product (3S,8S,10R,13R,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-
tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 3,4,5-trimethoxybenzoate. The synthesized compound has been
characterized by 1H NMR, 13C NMR, UV, FT-IR and mass spectroscopy. Density functional theory (B3YLP) using a 6-31G
(d,p) basis set has been used for quantum chemical calculations. The reactive site and reactivity within the molecule are
rendered by global and local reactivity descriptors, whereas AIM (Atom in a molecule) approach illustrated weak molecular
interactions within the molecule. The energies of HOMO and LUMO and frontier orbital energy gap are calculated by time
dependent DFT approach using the IEFPCM model. A small value for the HOMO-LUMO energy gap indicates easier
charge transfer within the synthesized compound. The nucleophilic and electrophilic reactivity is determined by MEP
(molecular electrostatic potential) studies. The values calculated for polarizability, dipole moment, and first
hyperpolarizability are used to depict the NLO (nonlinear optical) property of the synthesized compound.
 
Date 2022-12-15T05:29:06Z
2022-12-15T05:29:06Z
2022-12
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/61012
https://doi.org/10.56042/ijc.v61i12.69446
 
Language en
 
Publisher NIScPR-CSIR,India
 
Source IJC Vol.61(12) [Dec 2022]