The effect of dicationic surfactants on the hydrolysis of bis(4-nitrophenyl) ethyl phosphate in a borate buffer is studied. The presence of long-chain surfactants results in a significant (up to 50-fold) increase in the observed rate constant (k obs) of the process. The catalytic effect of micelles increases with increasing alkyl chain length due to the strengthening of binding of the reagents by micelles. The presence of two cationic centers in the surfactant molecule enhances the catalytic properties of micelles. The dependence ofk obs of hydrolysis of the substrate on the borate buffer concentration is studied. Alkaline hydrolysis is more sensitive to the added surfactant than the reaction involving borate ions.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
C. A. Bunton, L. B. Robinson, J. Schaak, and M. F. Stam,J. Org. Chem., 1971,36, 2346.
E. M. Menger and R. A. Persichetti,J. Org. Chem., 1987,52, 3451.
E. P. Tishkova, S. B. Fedorov, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izy. Akad. Nauk SSSR, Ser. Khim., 1991, 2630 [Bull. Acad. Sci. USSR, Div. Chem Sci., 1991,40, 2302 (Engl. Transl.)].
S. Matsumoto, H. Masuda, K. Iwata, and O. Mitsunobu,Tetrahedron Lett., 1973, 1733.
US Pat. 2922810;Chem. Abstrs., 1960,54, 9848c.
V. E. Bel'skii, L. S. Novikova, L. A. Kudryavtseva, and B. E. Ivanov,Zh. Obshch. Khim., 1978,48, 1512 [J. Gen. Chem. USSR, 1978,48 (Engl. Transl.)].
K. Martinek, A. K. Yatsimirsky, A. V. Levashov, and I. V. Berezin, inMicellization, Solubilization, and Microemulsions, Ed. K. L. Mittal, Plenum Press, New York, 1977.
I. S. Ryzhkina, L. A. Kudryavtseva, V. E. Bel'skii, I. E. Ismaev, V. I. Morozov, A. V. Il'yasov, and B. E. Ivanov,Zh. Obshch. Khim., 1990,60, 820 [J. Gen. Chem. USSR, 1990,60 (Engl. Transl.)].
S. B. Fedorov, R. I. Tarasova, L. R. Syrneva, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 196 [Bull. Acad. Sci. USSR, Div. Chem Sci., 1982,31, 185 (Engl. Transl.)].
V. E. Bel'skii, L. A. Kudryavtseva, O. M. Il'ina, and B. E. Ivanov,Zh. Obshch. Khim., 1979,49, 2470 [J. Gen. Chem. USSR, 1979,49 (Engl. Transl.)].
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1576–1580, September, 1994.
About this article
Cite this article
Tishkova, E.P., Kudryavtseva, L.A., Shagidullina, R.A. et al. Hydrolysis of bis(4-nitrophenyl) ethyl phosphate in micellar solutions of dicationic surfactants. Russ Chem Bull 43, 1488–1492 (1994). https://doi.org/10.1007/BF00697133
- micellar catalysis
- dicationic surfactants