Nucleophilic elimination rates of ethoxide, methoxide, and hydroxide ions in solvents containing dioxan

Abstract

The nucleophilic reactivity of a reagent describes its kinetic behaviour towards positive centres on a substrate molecule. When this positive or electrophilic centre is a proton, this definition appears to be one of a basicity. But basicity refers to a thermodynamic affinity for protons under equilibrium conditions. Hence correlations between nucleophilicity and basicity must be examined closely. This is particularly important in the bimolecular elimination of hydrogen halides by basic anions.