Abstract
1-Cetyl-3-(2-oximinopropyl)imidazolium, 1-cetyl-3-(2-oxaminoethyl-2-one)imidazolium, and 1-cetyl-3-(2-amino-2-oximinoethyl)imidazolium halides were synthesized.These compounds form in water solutions functional zwitter-ionic micelles as surfactants. The cleavage kinetics of 4-nitrophenyl diethyl phosphate, 4-nitrophenyl ethyl ethylphosphonate, and 4-nitrophenyl tosylate in micelles of the functional detergents and combined micelles of the functional detergents with cetyltrimethylammonium chloride are adequately described in a framework of a simple pseudophase distribution model, and the micellar systems of the detergents are typical α-nucleophilic reagents. An equation was suggested for quantitative estimation of the micellar effect of the surfactants that took into account the change in the nucleophilic and basic characteristics of the α-nucleophilic center of the detergent and also the influence of the reagents concentrating on transition of the reaction from the water into micelle phase. The maximum acceleration of the SN2-reaction in the micelles of the functional zwitter-ionic detergents for the cleavage of 4-nitrophenyl diethyl phosphate and 4-nitrophenyl tosylate reached 3500 and 75 000 (oximate surfactant), 3300 and 66 000 (amidoximate surfactant ), and 4800 and 12200 (hydroxamate surfactant) times respectively. New functional detergents underlie unique supernucleophilic micellar system affording extremely high cleavage rates of organophosphorus substrates-ecotoxicants.
Published Version
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