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5


Teoret. i eksperim. khimiya. 2006. Vol.42 No. 6. p. 357-363

Micellar Effects of Surfactants in Reaction of Cleavage
of 4-Nitrophenyl Diethylphosphonate by Hydroperoxide Anion

 

T. N. Solomoichenko, Yu. S. Sadovskii, T. M. Prokopieva, E. A. Karpichev,
I. V. Kapitanov, Zh. P. Piskunova, V. A. Savyolova, A. F. Popov


L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine
Vul. R. Luxemburg, 70, Donetsk 83114, Ukraine. Е-mail: euak@skif.net


Nucleophilicity of hydroperoxide anion towards 4-nitrophenyl diethylphosphonate (NPDEPS) in the presence of cetyltrimethylammonium bromide (water, 25 °C) was studied within wide range of acidity and hydroperoxide concentration. Increase in the rate of reaction at its transfer from water into micellar pseudophase reached ~10 times that is explained by the effects of concentrating. In CTABr micelles, as in water, hydroperoxide anion is one of the most efficient α-nucleophiles, and the value of α-effect characterized as the ratio of second-order reaction rates for reaction of HOO- and OH- anions with NPDEPS remains essentially constant and reaches ~50.


Key word nucleophilic substitution, 4-nitrophenyl diethylphosphonate, hydroperoxide anion, cetyltrimethyl-
ammonium bromide, micellar effects.