Abstract
The surface potential in aqueous micellar solutions of a series of cetyltrialkylammonium bromides containing a hydroxyalkyl fragment in the head group was determined with a spectral probe (p-nitrophenol). It was found that the catalytic effect exerted by these surfactants in solution on the base hydrolysis of carboxylic acid esters is determined by two factors. First, the charged nucleophile is concentrated at the micelle surface. Second, hydrogen bonding of the substrate with the hydroxyalkyl substituents results in its activation.
Similar content being viewed by others
References
Micellization, Solubilization, and Microemulsions, Mittal, K.L., Ed., New York: Plenum, 1977.
Morales-Rojas, H. and Moss, R.A., Chem. Rev., 2002, vol. 102, no. 7, p. 2497.
Vriezema, D.M., Aragones, M.C., Elemans, J.A.A.W., Cornelisstn, J.L.M., Rowan, A.E., and Nolte, R.J.M., Chem. Rev., 2005, vol. 105, no. 4, p. 1445.
Dwars, T., Paetzold, E., and Oehme, G., Angew. Chem. Int. Ed., 2005, vol. 44, no. 44, p. 7174.
Zakharova, L.Ya., Mirgorodskaya, A.B., Zhil’tsova, E.P., Kudryavtseva, L.A., and Konovalov, A.I., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, no. 7, p. 1331.
Zana, R. and Xia, J., Gemini Surfactants Synthesis, Interfacial and Solution-Phase Behavior, Applications, New York: Dekker, 2003.
Basu Ray, G., Chakraborty, I., Gosh, S., Moulik, S.P., and Palepu, R., Langmuir, 2005, vol. 21, no. 24, p. 10958.
Serdyuk, A.I. and Kucher, R.V., Mitsellyarnye perekhody v rastvorakh poverkhnostno-aktivnykh veshchestv (Micellar Transitions in Surfactant Solutions), Kiev: Naukova Dumka, 1987.
Mchedlov-Petrosyan, N.O., Differentsirovanie sily organicheskikh kislot v istinnykh i organizovannykh rastvorakh (Differentiation of the Strength of Organic Acids in True and Organized Solutions), Kharkov: Khar’k. Nats. Univ., 2004.
Mirgorodskaya, A.B., Kudryavtseva, L.A., Zakharova, L.Ya., and Bel’skii, V.E., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, no. 7, p. 1333.
Solntsev, K.M., Al-Ainain, S.A., Il’ichev, Y.V., and Kuzmin, M.G., J. Phys. Chem. A, 2004, vol. 108, no. 40, p. 8212.
Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases. A Laboratory Manual, New York: Wiley, 1962.
Berezin, I.V., Martinek, K., and Yatsimirskii, A.K., Usp. Khim., 1973, vol. 42, no. 10, p. 1729.
Das, D. and Das, P., Langmuir, 2003, vol. 19, no. 22, p. 9114.
Bhattacharya, S. and Snehalatha, K., J. Chem. Soc., Perkin Trans. 2, 1996, p. 2021.
Bunton, C.A., J. Am. Chem. Soc., 1973, vol. 95, no. 9, p. 2912.
Tishkova, E.P., Fedorov, S.B., Kudryavtseva, L.A., Bel’skii, V.E., and Ivanov, B.E., Zh. Obshch. Khim., 1990, vol. 60, no. 10, p. 2256.
Menger, F.M. and Portnoy, C.T., J. Am. Chem. Soc., 1968, vol. 90, no. 7, p. 1875.
Bunton, S.A. and Savelli, G., Adv. Phys. Chem., 1986, vol. 22, p. 213.
Zakharova, L.Ya., Fedorov, S.B., Kudryavtseva, L.A., Bel’skii, V.E., and Ivanov, B.E., Izv. Ross. Akad. Nauk, Ser. Khim., 1993, no. 7, p. 1396.
Zakharova, L.Ya., Kudryavtsev, D.B., Kudryavtseva, L.A., Konovalov, A.I., Zuev, Y.F., Vylegzhanina, N.N., Zakhartchenko, N.L., and Idiyatullin, Z.Sh., Mendeleev Commun., 1999, no. 6, p. 245.
Aswal, V.K. and Goyal, P.S., Phys. Rev. E, 1999, vol. 59, no. 3, p. 3116.
Shinoda K., Nakagawa, T., Tamamushi, B.-i., and Isemura, T., Colloidal Surfactants: Some Physicochemical Properties, New York: Academic, 1963.
Zakharova, L.Ya., Kudryavtsev, D.B., Kudryavtseva, L.A., Zuev, Yu.F., Zakharchenko, N.L., Vylegzhanina, N.N., Idiyatullin, Z.Sh., and Fedotov, V.D., Zh. Obshch. Khim., 2002, vol. 72, no. 3, p. 458.
Zakharova, L.Ya., Kudryavtsev, D.B., Valeeva, F.G., and Kudryavtseva, L.A., Zh. Obshch. Khim., 2002, vol. 72, no. 8, p. 1296.
Mirgorodskaya, A.B., Kudryavtseva, L.A., Pankratov, V.A., Lukashenko, S.S., Rizvanova, L.Z., and Konovalov, A.I., Zh. Obshch. Khim., 2006, vol. 76, no. 10, p. 1696.
Chatterjee, A., Maiti, S., Sanyal, S.K., and Moulik, S.P., Langmuir, 2002, vol. 18, no. 8, p. 2998.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.B. Mirgorodskaya, L.R. Bogdanova, L.A. Kudryavtseva, S.S. Lukashenko, A.I. Konovalov, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 2, pp. 179–186.
Rights and permissions
About this article
Cite this article
Mirgorodskaya, A.B., Bogdanova, L.R., Kudryavtseva, L.A. et al. Role of surface potential in the catalytic action of micelles of cationic surfactants with a hydroxyalkyl fragment in the head group. Russ J Gen Chem 78, 163–170 (2008). https://doi.org/10.1134/S1070363208020023
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363208020023