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First principle study of the structure of conjugated amides and thioamides
Author(s) -
Velkov Zhivko,
Velkov Yasen,
Balabanova Elena,
Tadjer Alia
Publication year - 2006
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21234
Subject(s) - thioamide , conjugated system , chemistry , delocalized electron , amide , density functional theory , computational chemistry , ab initio , quantum chemical , electron delocalization , stereochemistry , organic chemistry , molecule , polymer
On the basis of ab initio and density functional theory (DFT) calculations of the o ‐coumaric amide and thioamide, the latter is found to have better delocalization. It is demonstrated that the thioamide function features stronger attraction for electron density from the conjugated residue. Therefore, the electronic distribution in the thioamide favors stable phenoxyl radical formation. This is a reason to expect better antioxidant activity of the thioamide. © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2007