Quantitative characterization of the global philicity patterns of common diene/dienophile pairs in cycloaddition reactions II: the interacting pair model

Abstract

We present a unified model of electrophilicity and nucleophilicity that considers the electrophile/nucleophile pair in an interacting regime, thereby avoiding the arbitrariness of defining them as the opposite ends of a unique reactivity scale. The model is validated against rate coefficients for the cycloaddition of azomethine ylides towards substituted acetylenes and Michael addition of a series of 1-(X-substituted phenyl)-2-propyn-1-ones towards hydrazine.