A mechanistic study of the reaction between aryldiazonium ions and imidazoles

Abstract

Whereas the neutral form of pyrrole reacts with 4-nitrobenzenediazonium ions, the parallel reaction of imidazole involves the anion. The involvement of the imidazole anion is based on kinetic evidence, pressure studies, and MNDO calculations. N-Methylation affects not only the kinetics of reaction but also the products. With the neutral form of imidazole it is suggested that the predominant reaction with an aryldiazonium ion is reversible attack on a ring nitrogen.