Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane

Abstract

The rate constants for the reaction of twenty-two N-(substituted phenylmethylene)- m- and -p-aminobenzoic acids with diazodiphenylmethane were determined in absolute ethanol at 30 °C. The effects of substituents on the reactivity of the investigated compounds were interpreted by correlation of the rate constants with LFER equations. The results of quantum mechanical calculations of the molecular structure together with experimental results gave a better insight into the effects of structure on the transmission of electronic effects of the substituents. New σ constants for substituted benzylideneamino group were calculated.

Keywords

• rate constants
• substituent and structural effects
• geometry optimization