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: email@example.com
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.
nucleophilic substitution, 4-nitrophenyl diethylphosphonate, hydroperoxide anion, cetyltrimethyl-
ammonium bromide, micellar effects.