Substituent Electronic Effects on the Mulliken Charges of N-(4-Substituted Benzylidene)-1-Phenylmethanamine Oxide Elucidated by DFT Calculations

Abstract

Calculations based on density functional methods are carried out to investigate the effects of a variety of substituents (NMe 2 , OMe, Me, F, H, Cl, CN, NO 2 ) on the Mulliken charges (Q M ) for C α and N atoms of N-(4-Substituted benzylidene)-1-phenylmethanamine oxide using Hammett's MSP and Taft's DSP equations. The MSP and DSP correlations give normal substituent effect at C α and N atom sites. This can be attributed to extended π-polarization, which predominates over the localized π-polarization.