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Journal of the Serbian Chemical Society 2004 Volume 69, Issue 11, Pages: 877-882
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Geometry and conformation of benzenecarboxylic acids

Marković Zoran, Bajduk Dalibor, Gutman Ivan

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.

Keywords: benzenecarboxylic acids, phthalic acid, trimesic acid, conformation, rotamer