Reactivity of N-alkyl derivatives of hydroxylamine in decomposition of 4-nitrophenyl diethylphosphonate in water and in cetyltrimethylammonium bromide micelles

• DOI: 10.1007/s11237-007-0029-8
• Publication Date: 2007-10-05T14:59:05Z
• Authors: T. M. Zubareva; T. M. Prokop’eva; I. V. Kapitanov; I. A. Belousova; N. G. Razumova; A. F. Popov
• Keywords: 01 natural sciences; 0104 chemical sciences

Neutral forms of hydroxylamine, N-methylhydroxylamine, and N,N-dimethylhydroxylamine are typical α-nucleophiles in water. In comparison with aryl anions of similar basicity their rate of reaction in the decomposition of 4-nitrophenyl diethylphosphonate is increased by about 102 times. Decomposition of the substrate is accelerated in cetyltrimethylammonium bromide micelles (about 4 to 30 fold). Hydroxylamine and its N-alkyl derivatives are the most effective low basicity nucleophiles. The sole factor responsible for the micellar effects is the concentration of the reagent in the surfactant micelles.