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Teoret. i eksperim. khimiya. 2004. Vol.40 No. 5. p. 291-297

Trihalide Organocomplexes as α-Nucleophiles and Efficient Oxidizers in Decomposition
of Organophosphorus Compounds in Water and in Micelles of Surfactants


V. A. Savyolova, C. A. Bunton*, T. M. Prokop³eva, M. K. Turovskaya, E. A. Karpichev,
V. A. Mikhailov, A. L. Kanibolotskii, N. I. Burakov, 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: euak@skif.net

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

The nucleophilic and oxidizing reactivity of HOBr/BrO- system toward 4-nitrophenyl diethyl phosphate, 4-nitrophenyl-4'-toluenesulfonate (nucleophilic substitution) and 4-nitrophenol (oxidation) was studied in water and in micelles of neutral, cationic and anionic surfactants. Trihalide organocomplexes were used as a source of «active» bromine. Micellar effects of surfactants in nucleophilic substitution were adequately described by both pseudo-phase partitioning and ion exchange models. Only cationic surfactants give rise to 20-30 fold increase in the observed reaction rates of BrO- ion with esters and 5-fold increase for HOBr with nitrophenol and the system HOBr/BrO- is among the most efficient in decomposition of organophosphorus compounds.

Key word trihalide organocomplexes, nucleophilic substitution, oxidation, organophosphorus compounds, surfactants.