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Teoret. i eksperim. khimiya. 2004. Vol.40 No. 3. p. 150-156

Supernucleophilic Reactivity of Hypobromite Ion towards
to 4-Nitrophenyl Diethyl Phosphonate in Water and in Micelles
of Cetyltrimethylammonium Bromide


Yu. S. Simanenko, T. M. Prokopieva, C. A. Bunton*, V. A. Savyolova,
M. K. Turovskaya, E. A. Karpichev, V. A. Mikhailov, A. F. Popov

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

* Department of Chemistry and Biochemistry, University of California
Santa Barbara, California, 93106, USA

Nucleophilic reactivity of a typical α-nucleophile - hypobromite ion generated by organocomplexes of tribromide ions with respect to 4-nitrophenyl diethyl phosphonate in water and micelles of cetyl- trimethylammonium bromide (CTABr) was studied. The BrO--CTABr system is one of the most effective for decomposition of organophosphorous compounds: the effect of reagent concentrating ensures quick decomposition of 4-nitrophenyl diethyl phosphonate in aqueous micellar medium with t1/2 ≤ 20 s (t1/2 600 s in water).

Key words reactivity, hypobromite ion, 4-nitrophenyl diethyl phosphonate, surfactants.