Mechanistic duality of the side-chain substitution in electrophilic aromatic nitration. Unexpected large difference in deuterium isotope effect kH/ kD between the side-chain nitration and nitrooxylation of deuterated p-xylenes

Abstract

A large difference in deuterium kinetic isotope effect observed between the side-chain nitration and nitrooxylation of deuterated p-xylenes, 1,4-(CH 3)(CD 3)C 6H 4 and 1,4-(CD 3) 2C 6D 4, suggests the operation of different mechanisms for these two types of side-chain substitution.