Abstract
The formation of surfactant-hydrophobic amine mixed aggregates reduces the pK a of long-chain amines by 1–1.5 units compared with those in molecular solutions and is an important factor responsible for the high catalytic effect of the system in ester bond cleavage. In aqueous solution of geminal surfactants, the rate of azomethine formation in the reaction of long-chain amines with benzaldehydes is an order-of-magnitude higher than in ethanol.
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Micellization, Solubilization and Microemulsions, Mittel, K.L., Ed., New York: Plenum, 1978.
Bunton, S.A. and Savelli, G., Adv. Phys. Chem., 1986, vol. 22, p. 213.
Dwars, T., Paetzold, E., and Oehme, G., Angew. Chem. Int. Ed., 2005, vol. 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.
Menger, F.M. and Keiper, J.S., Angew. Chem., 2000, vol. 112, p. 1980.
Hait, S.K. and Moulik, S.P., Current Sci., 2002, vol. 82, no. 10, p.1101.
Groth, C., Nyden, M., Holmberg, R., Kanicky, J.R., and Shah, D.O., J. Surf. Deterg., 2004, vol. 7, no. 3, p. 247.
Zana, R., J. Colloid Interface Sci., 2002, vol. 248, no. 2, p. 203.
Aswal, V.K., De, S., Goyal, P.S., Bhattacharya, S., and Heenan, R.K., Phys. Rev. E, 1998, vol. 57, no. 1, p. 776.
Siddiqui, U.S., Ghosh, G., and Kabir-ud-Din, Langmuir, 2006, vol. 22, no. 24, p. 9874.
Borse, M.S. and Devi, S., Adv. Colloid Interface Sci., 2006, vols. 123–126, p. 387.
Bhattacharya, S. and Kumar, V.P., J. Org. Chem., 2004, vol. 69, no. 2, p. 559.
Bhattacharya, S. and Kumar, V.P., Langmuir, 2005, vol. 21, no. 1, p. 71.
Geng, Y., Romsted, L. S., and Menger, F., J. Am. Chem. Soc., 2006, vol. 128, no. 2, p. 492.
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.
Sekhon, B.S., Resonance, 2004, no. 3, p. 42.
Mirgorodskaya, A.B., Kudryavtseva, L.A., Zuev, Yu.F., Arkhipov, V.P., Idiyatullin, Z.Sh., and Kudryavtsev, D.B., Izv. Akad. Nauk., Ser. Khim., 2000, no. 2, p. 267.
Mirgorodskaya, A.B., Kudryavtseva, L.A., Zuev, Yu.F., and Vylegzhanina, N.N., Zh. Fiz. Khim., 2002, vol. 76, no. 11, p. 2049.
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.
Mirgorodskaya, A.B., Kudryavtseva, L. A., and Ivanov, B.E., Izv. Ross. Akad. Nauk, Ser. Khim., 1996, no. 2, p. 366.
Babic, K., van der Ham, L., and de Haan, A., React. Funct. Polym., 2006, vol. 66, no. 12, p. 1494.
Nesmeyanov, A.N. and Nesmeyanov, N.A., Nachala organicheskoi khimii (Fundamentals of Organic Chemistry), Moscow: Nauka, 1970.
Doronin, S.Yu., Chernova, R.K., and Gusakova, N.N., Zh. Anal. Khim., 2005, vol. 60, no. 5, p. 471.
Chernova, R.K., Doronin, S.Yu., and Myznikova, I.V., Khim. Tekhnol., 2005, vol. 48, no. 6, p. 113.
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Original Russian Text © A.B. Mirgorodskaya, L.A. Kudryavtseva, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 1, pp. 44–50.
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Mirgorodskaya, A.B., Kudryavtseva, L.A. Aqueous solutions of geminal alkylammonium surfactants as a medium for reactions of long-chain amines. Russ J Gen Chem 79, 42–48 (2009). https://doi.org/10.1134/S1070363209010071
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DOI: https://doi.org/10.1134/S1070363209010071