Some observations relating to substituent effects in halogenation. Part II. The reaction of m- and p-chloroacetanilide with chlorine in acetic acid

Abstract

The rates of chlorination by molecular chlorine of m- and p-chloroacetanilide have been measured at 25° in acetic acid as solvent. The proportions of isomers obtained under these conditions have also been estimated, and enable calculation of the partial rate factors in the various positions. The results are discussed in terms of the “additivity principle,” that is by assuming that the influence of substituents is independent and additive in the free energy of activation.