Abstract
The influence of a number of electrolytes on the micellar effect of cetyltrimethylammoniurn bromide (CTAB) in the hydrolysis ofp-nitrophenyl acetate (1) and bis(p-nitrophenyl) methylphosphonate (2) and in the course of the acid-base dissociation of thep-nitroanilide of bis(chloromethyl)phosphinic acid (3) has been examined. The activity of the salts studied increases in the following order: MeCOOK<K2CO3<KCl<KBr<KNO3<p-MeC6H4SO3K. It has been found that in the presence of electrolytes the catalytic effect of CTAB micelles in the hydrolysis reactions of esters1 and2 decreases, and the pK a value of anilide3 increases. The results obtained are interpreted in terms of the pseudophase model of micellar catalysis. The analysis of the experimental data carried out using logarithmic coordinates revealed a relationship between phase transitions in micellar catalysis and in micellization.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. Ya. Zakharova, S. B. Fedorov, L. A. Kudryavtseva, A. M. Zotova, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2161 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 2003 (Engl. Transl.)].
E. P. Tishkova, L. Ya. Zakharova, O. M. Il'ina, and S.B. Fedorov,Khimiya i tekhnologiya elementoorganicheskikh soedinenii i polimerov [Chemistry and Technology of Organoelement Compounds and Polymers],Mezhvus. sb., Kazan', 1988, 42 (in Russian).
K. Martinek, A. K. Yatsimirsky, A. V. Levashov, and I.V. Berezin, inMicellization, Solubilization, and Microemulsions, Ed. K. L. Mittal, Plenum Press, New York-London, 1977.
L. S. Romsted, inMicellization, Solubilization, and Microemulsions, Ed. K. L. Mittal, Plenum Press, New York-London, 1977.
L. S. Romsted and E. N. Cordes,J. Am. Chem. Soc., 1968,90, 4404.
L. Ya. Zakharova, S. B. Fedorov, L. A. Kudryavtseva, V. E. Bel'skii, A. B. Mirgorodskaya, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1718 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1555 (Engl. Transl.)].
E. J. Berhman, M. J. Biallas, H. J. Brass, J. O. Edwards, and M. Isaks,J. Org. Chem., 1970,35, 3063.
L. Ya. Zakharova, S. B. Fedorov, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990,991 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 883 (Engl. Transl.)].
J. E. Gordon,The Organic Chemistry of Electrolyte Solutions, Wiley-Interscience, New York-London-Sydney-Toronto, 1975.
N. Mazer, M. Keri, and J. B. Benedek, inMicellization, Solubilization, and Microemulsions, Ed. K. L. Mittal, Plenum Press, New York-London, 1977.
T. Imae and S. Ikeda,J. Colloid and Polym. Sci., 1987,265, 1090.
R. Zielinski, S. Ikeda, N. Nomera, and S. Kate,J. Colloid and Interface Sci., 1988,125, 497.
G. Porte and J. Appell, inSurfactants in Solution, Ed. K. L. Mittal, 1984,2, 805.
M. P. S. Novel, D. Zanette, F. Quina, M. T. Moretti, and F. Nome,J. Phys. Chem., 1989,93, 1502.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1396–1400, August, 1993.
Rights and permissions
About this article
Cite this article
Zakharova, L.Y., Fedorov, S.B., Kudryavtseva, L.A. et al. The effect of electrolytes on the reaction rates and acid-base equilibria in ionic micelles. Russ Chem Bull 42, 1329–1333 (1993). https://doi.org/10.1007/BF00699925
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00699925