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

The rate constants for the reaction of twenty-two N-(substituted phenyl- methylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane were deter- mined 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 mole- cular structure together with experimental results gave a better insight into the ef- fects of structure on the transmission of electronic effects of the substituents. New σ constants for substituted benzylideneamino group were calculated.