Acid catalysis of carbon–hydrogen bond-breaking in α-heterocyclic ketones: a Brönsted treatment of catalyst binding and reactivity

Abstract

The relative effectiveness of O- and N-protonation in catalysing C–H bond-breaking in α-heterocyclic ketones is described by an equation based on rapid binding of catalyst to substrate and a Brönsted-Marcus treatment of the catalytic steps; the equaitoin shows that efficient catalysis reflects strong binding of the catalyst to both the reactant and the product of the uncatalysed reaction.