Predicting the reactivity of ambidentate nucleophiles and electrophiles using a single, general-purpose, reactivity indicator

We recently proposed a new reactivity indicator, termed the "general-purpose reactivity indicator", Xi, which describes not only the classical reactivity paradigms, but also describes reactions that are neither frontier-orbital nor electrostatically controlled. This indicator was proposed to be especially useful for reactants with multiple reactive sites, especially if the nature of the reactivity at those sites was different. This suggests …