Aromaticity of bent benzene rings: A VBSCF study

Abstract

The effect of ring deformation on aromaticity has been studied for bent benzene molecules in which two carbon atoms have been bent out of plane, resulting in a boat conformation. Valence-bond self-consistent field (VBSCF) calculations have been performed on these molecules to obtain insight into the aromaticity of bent benzenes. Results for total energy, structure energies, weights, and orbital overlaps show that the molecule keeps its aromatic nature up to 55°. After 55° a transition to Dewar benzene occurs. The valence-bond model, by showing the weights of both Dewar and Kekulé structures, is an excellent tool to study deformed benzene. ©1999 John Wiley & Sons, Inc. Int J Quant Chem 74: 213–221, 1999