Theoretical Study on the Substituent Effects Stabilizing Benzylic Anions

Abstract

Substituent effects on the stabilities of benzylic cations are well described by the Yukawa-Tsuno equation which devide the electronic effects of substituents to inductive and resonance effects. While, anionic systems are not easy to analyze due to significant solvent effects. We clarified that the specific hydration to the ring substituents play an important role to determine the acidities of phenols in aqueous media. This work is to make clear the intrinsic effect of ring substituents of anions in the gas phase. Gas phase stabilities of benzylic anions included electronically various substituents are determined using molecular orbital calculations. Substituent effects of anion systems are compared one another to discuss what kind of effects are important to determine the stabilities of anions.