Acid- and base-catalyzed deuterium-protium exchange of some polyazaindenes

Abstract

The acid-catalyzed deuterium-protium exchange of compounds 1, 2, and 3 occurs at the positions typical for electrophilic substitutions.These substitutions are shown to occur on the free bases. The base-catalyzed deuterium-protium exchange of compounds 1, 2, and 3 occurs at positions adjacent to nitrogen atoms which possess a partial positive charge as indicated by major resonance contributing structures. Proton transfer is shown to be involved in the rate-determining step.