Structure–reactivity correlations for aza‐arenes. Proton affinities, pKa values, hydrogen–deuterium exchange rates and radical‐induced 13C shifts

Abstract

AbstractMolecular reactivity parameters based on the concept of an effective electronic potential and defined as a simple function of the molecular charge distribution were applied in a study of various aspects of the chemical reactivity of azabenzenes and azanaphthalenes. Excellent linear correlations were obtained for proton affinities, pKa values, H–D exchange rate exponents and 13C shifts induced by the paramagnetic shift reagent TEMPO. In the last case, the predictions for quinazoline prompted a reinvestigation of the 13C NMR spectrum of this compound, resulting in a reassignment of the spectrum relative to the assignment assumed by Grant and co‐workers.