Some observations relating to substituent effects in halogenation. Part IV. Reaction of o- and p-nitroacetanilide with chlorine in acetic acid

Abstract

The reactivities of o-, m-, and p-nitroacetanilide with molecular chlorine in acetic acid at 25° have been investigated and compared with those of benzene and acetanilide under the same conditions. The proportions of isomers formed in the chlorination of o-nitroacetanilide have been determined by vapour-phase chromatography. From the relative rates and product compositions partial rate factors have been calculated. By comparison with the partial rate factors for chlorination of acetanilide, indirect estimates of the directive influence of the nitro-group in the meta-position have been evaluated. The results obtained, together with those estimated for the same substituent from data for other sets of reactions, are discussed in terms of the additivity principle.