Open AccessGeometry and conformation of benzenecarboxylic acids
Author(s) -
Zoran Marković,
Dalibor Bajduk,
Iván Gutman
Publication year - 2004
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc0411877m
Subject(s) - terephthalic acid , conformational isomerism , benzene , chemistry , ring (chemistry) , isophthalic acid , group (periodic table) , benzoic acid , carboxylic acid , planar , phthalic acid , trimesic acid , stereochemistry , crystallography , polymer chemistry , molecule , organic chemistry , polyester , computer graphics (images) , computer science
The geometry, conformations and energy of mono-, di-, and tri-carboxylic derivatives of benzene were studied by means of the AM1 molecular-orbital method. Whereas the species having no carboxylic groups in the ortho-position (benzoic, isophthalic, terephthalic, and trimesic acids) are planar in all their (stable) conformations, those possessing carboxylic groups in the ortho-position (phthalic, 1,2,3-benzenetricarboxylic, and 1,2,4-benzenetricarboxylic acids) assume a non-planar geometry, with one carboxyl group almost orthogonal to the plane of the benzene ring. Various rotamers of each of the studied benzenecarboxylic acids have nearly the same energy.