A Comparative investigation of the nucleophilic reactivities of hydroxide and phenoxide ions

Abstract

In considering the rates of bimolecular nucleophilic substitution and elimination reactions, it has been a common practice to draw analogies between the nucleophilic character of the reagent and its basicity. If basicity can be considered to be a measure of nucleophilicity then the sequences OH-, OPh-, OAc-, Cl- or OR-, SR-, SeR- should correspond to a decreasing nucleophilic strength, just as they do to a decreasing basic strength. Since, however, the basicity of a reagent is its nucleophilic affinity for hydrogen ions