The reactivity of phosphate esters. Diester hydrolysis
Phosphate diesters are, in general, exceedingly unreactive compounds, but their reactivity towards hydrolysis depends strongly on the basicity of the leaving group. As a result the difference in reactivity between diester and monoester monoanions decreases rapidly as the basicity of the leaving group decreases, and with very good leaving groups the reactivity of the two classes of compounds is comparable. The mechanism of hydrolysis of phosphate diester anions appears to involve bimolecular nucleophilic attack of solvent on phosphorus.