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Updated: May 7, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
2-(2-Methyl-benzo-yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
Natalia A Platosz1, Roger A Lalancette, Hugh W Thompson
1Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102 , USA.
Abstract:
The crystal structure of the title compound, C15H12O3, displays catemeric aggregation involving O-H⋯O hydrogen bonds progressing from the carboxyl group of one mol-ecule to the ketone O atom of another glide-related neighbor. The mol-ecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The mol-ecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along [001] in an A-A-B-B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related mol-ecule.
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