Linear solvation energy relationship in the reaction between phenacyl bromide and N-methyl aniline

The reaction between phenacyl bromide and N-methyl aniline has been studied conductometrically in 17 different protic and aprotic solvents. The reaction is overall second order, being first order with respect to each reactant. Correlation of the second order rate constants with different solvent parameters indicates that the solvation of the reactants and the transition state is due to non-specific polarity of the solvent, hydrogen bond donor ability, solvent nucleophilicity, and electrophilicity of the solvent. By statistical analysis, a linear solvation energy relationship is derived and the percentage contribution of each type of solvation is estimated.