Molecular structure, reactivity, and toxicity of the complete series of chlorinated benzenes.

J Phys Chem A 109(48):11043-9 (2005) PMID 16331949

The structure and chemical reactivity profiles of all 12 chlorobenzenes have been investigated using the density functional theory and ab initio molecular orbital calculations. Global and local reactivity descriptors such as electrophilicity index and local philicity, respectively, of the selected systems have been calculated in order to gain insights into the reactive nature and the reactive sites of these compounds. Also, the effects of chlorine substitution on the aromaticity of the compounds have been analyzed by calculating the nucleus-independent chemical shift. Interaction through charge transfer between chlorobenzenes and nucleic acid bases/selected base pairs are determined using Parr's formula. The results revealed that the chlorobenzenes act as electron acceptors in their interaction with biomolecules. Structure-toxicity analysis of this entire set of chlorobenzenes demonstrates the importance of the electrophilicity index in the prediction of reactivity/toxicity.