An AB initio comparative study of the electronic properties of sulfonamides and amides

Abstract

A comparative ab initio study of amides and sulfonamides has been carried out using minimal, extended and polarization basis sets. Rotational barriers and tautomerism are discussed comparatively. The two main conclusions of this study are the absence in sulfonamides of a conjugation of the type present in planar amides and the relative insensitivity of the total energy to nitrogen hybridization in sulfonamides in contrast with amides.