Reactivity of N-alkyl derivatives of hydroxylamine in decomposition of 4-nitrophenyl diethylphosphonate in water and in cetyltrimethylammonium bromide micelles |
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Authors: | T. M. Zubareva T. M. Prokop’eva I. V. Kapitanov I. A. Belousova N. G. Razumova A. F. Popov |
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Affiliation: | (1) L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Vul. R. Luxemburg, 70, Donets’k, 83114, Ukraine |
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Abstract: | 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. __________ Translated from Teoreticheskaya i éksperimental’naya Khimiya, Vol. 43, No. 4, pp. 231–236, July–August, 2007. |
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Keywords: | N-alkylhydroxylamines 4-nitrophenyl diethylphosphonate nucleophilic substitution cetyltrimethylammonium bromide micellar effects |
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