Kinetics and mechanism of electrophilic substitution of heteroaromatic compounds. Part XXIII. Acid-catalysed hydrogen exchange of quinoline, isoquinoline, and their N-oxides

Abstract

Rate profiles are reported for the title reactions. Exchanges are shown to proceed on the conjugate acid species at various positions in the carbocyclic rings. Exchange in the heterocyclic rings occurs by deprotonation α to nitrogen, and probably via covalent hydrated species β to nitrogen.