Hydrolytic Reactivity of an Active Synthetic C-N-P Ester Leading to its Highly Basic Nature

Abstract

Hydrolysis of synthetic bis-(m-MeO-phenyl) phosphoricamide chloride when performed in the acid range, 0.01-7.0 M HCl at 40 (± 0.5) ºC in 4 % AcOH-H₂O medium gives 1st-order rate coefficients. Ionic strength effect study reveals the contribution of: neutral better named here as protonated-neutral species (0.01-0.10 M HCl) and conjugate acid species (0.5-7.0 M HCl) showing a regular rate increase even between 4.0-7.0 M HCl. The latter behaviour is assigned to the highly basic nature of the present member, making it comparable to the strongly basic amides. The hydrolysis is remarkably promoted by the action of nucleophilic bromide ions [S_E2(P)].