Micellar effects of surfactants in cleavage of 4-nitro-phenyl diethyl phosphonate by hydroperoxide anion |
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Authors: | T. N. Solomoichenko Yu. S. Sadovskii T. M. Prokop’eva E. A. Karpichev I. V. Kapitanov Zh. P. Piskunova V. A. Savelova 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. Luxsemburg, 70, Donets’k, 83114, Ukraine |
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Abstract: | We have studied the nucleophilicity of the hydroperoxide anion relative to 4-nitrophenyl diethyl phosphonate (NPDEPS) in the presence of cetyltrimethylammonium bromide (water, 25 °C) while varying the acidity of the medium and the hydroperoxide anion concentration over a broad range. The increase in the reaction rate when the reaction is transferred to a micellar pseudophase is as high as ∼10-fold, which is explained by concentration effects. In CTAB micelles, as in water, the hydroperoxide ion is one of the most effective α-nucleophiles, and the size of the α-effect, characterized by the ratio of the second-order rate constants for reactions of HOO− and OH− anions with NPDEPS, remains practically constant and reaches a value of ∼50-fold. __________ Translated from Teoreticheskaya i éksperimental’naya Khimiya, Vol. 42, No. 6, pp. 357–363, November–December, 2006. |
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Keywords: | nucleophilic substitution 4-nitrophenyl diethyl phosphonate hydroperoxide anion cetyltrimethylammonium bromide micellar effects |
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