Conformation of hydrogen-bonded dimeric o-methyl-substituted benzoic acids

Acta Crystallogr C. 2008 Apr;64(Pt 4):o208-10. doi: 10.1107/S0108270108005799. Epub 2008 Mar 8.

Abstract

Molecules of 2,4-dimethylbenzoic acid, C(9)H(10)O(2), form typical centrosymmetric hydrogen-bonded dimers. The carboxyl group is twisted with respect to the benzene ring and the methyl group in the ortho position shows evasive in-plane splaying. The relation between the in-plane splaying and the twist angle of the carboxyl group for various ortho-substituted dimeric derivatives of benzoic acid is presented. It shows how the steric strains are released depending on the numbers and positions of the substituents.