Geometry and conformations of benzenecarboxylic acids

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...

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Bibliographic Details
Main Authors: IVAN GUTMAN, DALIBOR BADJUK, ZORAN MARKOVIC
Format: Article
Language:English
Published: Serbian Chemical Society 2004-11-01
Series:Journal of the Serbian Chemical Society
Subjects:
Online Access:http://www.shd.org.yu/HtDocs/SHD/Vol69/No11/V69-No11-06.pdf
Description
Summary: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.
ISSN:0352-5139