1. bookVolume 10 (2017): Issue 2 (December 2017)
Journal Details
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Journal
eISSN
1339-3065
First Published
10 Dec 2012
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2 times per year
Languages
English
access type Open Access

Quantum-chemical study of molecular structure and relative stability of trans and cis isomers of model anilide derivatives

Published Online: 29 Dec 2017
Volume & Issue: Volume 10 (2017) - Issue 2 (December 2017)
Page range: 144 - 151
Journal Details
License
Format
Journal
eISSN
1339-3065
First Published
10 Dec 2012
Publication timeframe
2 times per year
Languages
English
Abstract

Derivatives of anilide were studied systematically by the density functional theory (DFT) using the B3LYP hybrid functional and the 6-311+G(3df,2p) basis set. Characteristic frequencies of N-H and C=O stretching modes for cis and trans conformers distinguishing were compared with available experimental and theoretical data. Effect of substitution in ortho position and acidic residue group is discussed with respect to the bond length changes in the aromatic ring and aromaticity indexes. Energy differences between cis and trans conformations allow estimating the effect of intramolecular hydrogen bonds stabilizing the studied conformations. The trans conformation of parent formanilide is stabilized via the C(aromatic) -H∙∙∙O=C interaction with the energy of around 4 kJ・mol-1. The selected anilide series represent model compounds for drug design.

Keywords

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