Nucleophilic attack at the pyridine nitrogen atom in a bis(imino)pyridine system: The local hard and soft acids and bases principle perspective

Abstract

Motivated by the unprecedented nucleophilic attack at the pyridine nitrogen atom in bis(imino)pyridines, observed by Gambarotta et al. and Gibson et al., and the fact that normally pyridine undergoes reactions with electrophiles at its nitrogen atom, we applied the local hard and soft acids and bases principle to assert that nucleophilic attack at pyridine nitrogen atom depends fundamentally on stereoelectronic factors. © 2012, Sociedad Química de México.