Mechanism of nucleophilic substitution in O,O-dimethyl-O-(4-nitrophenyl)thiophosphate in micellar solutions of 2-hydroxyethyldimethyloctadecylammonium bromide

Abstract

The mechanism of nucleophilic substitution in O,O-dimethyl-O-(4-nitrophenyl)-thiophosphate (DNTP) has been studied in alkaline micellar solutions of cationic 2-hydroxyethyl surfactant which displays nucleophilic properties on account of dissociation of the 2-hydroxyethyl group. Further transformation of the intermediate product formed can take place by regeneration of the initial nucleophilic form of the surfactant, or by formation of a new zwitterion form of phosphorylated surfactant.