The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XXIX. The nitration of the 1-methyl cations of 2-methylamino-, 2-methylamino-5-nitro-, and 4-dimethylamino-pyridine

Abstract

Rate constants for the nitration of the title compounds have been determined and compared with those for 2-dimethylamino-, 2-dimethylamino-5-nitro-, and 4-dimethylamino-pyridine. The mechanisms of nitration of these substituted pyridines is discussed with particular reference to the occurrence of the ‘proton loss’ mechanism.