Abstract
The rate of carboxylic ester cleavage by amphiphilic low-molecular-weight and polymeric amines in the presence of polyoxyethylated calix[4]arenes with different degrees of oxyethylation is determined by the formation of mixed aggregates, by the shift of pK a of the amine, and the character of the distribution of the reactants in functional micelles. All of the systems show a high substrate specificity. In the case of octyl- and decylamines, the reaction of p-nitrophenyl acetate is catalyzed and the reaction of more hydrophobic p-nitrophenyl laurate is inhibited. An opposite situation is observed in the systems based on branched polyethyleneimine: the reaction of p-nitrophenyl acetate is inhibited and the process involving p-nitrophenyl laurate is accelerated.
Similar content being viewed by others
References
Fendler, J.H., Chem. Rev., 1987, vol. 87, no. 5, p. 877.
Chang, G.G., Huang, T.M., and Hung, H.C., Proc. Natl. Sci. Counc. Repub. China B, 2000, vol. 24, no. 3, p. 89.
Vriezema, D.M., Aragons, M.C., Elemans, J.A.A.W., Cornelissen, J.J.L.M., Rowan, A.E., and Nolte, R.J.M., Chem. Rev., 2005, vol. 105, no. 4, p. 1445.
Berezin, I.V., Martinek, K., and Yatsimirskii, A.K., Usp. Khim., 1973, vol. 42, no. 10, p. 1729.
Bunton, C.A. and Savelli, G., Adv. Phys. Org. Chem., 1986, vol. 22, p. 213.
Micellization, Solubilization, and Microemulsion, Mittel, K., Ed., New York: Plenum, 1977.
Dwars, T., Paetzold, E., and Oehme, G., Angew. Chem. Int. Ed., 2005, vol. 44, p. 7174.
Khan, M.N., Micellar Catalysis, New York: CRC, 2006.
Zakharova, L.Ya., Mirgorodskaya, A.B., Zhiltsova, E.P., Kudryavtseva, L.A., and Konovalov, A.I., Molecular Encapsulation: Organic Reactions in Constrained Systems, Brinker, U.H. and Mieusset, J.-L., Eds., Chichester: Willey, 2010, p. 397.
Mustafina, A., Zakharova, L., Elistratova, J., Kudryashova, J., Soloveva, S., Garusov, A., Antipin, I., and Konovalov, A., J. Colloid Interface Sci., 2010, vol. 346, no. 2, p. 405.
Zakharova, L., Kudryashova, Y., Selivanova, N., Voronin, M., Ibragimova, A., Solovieva, S., Gubaidullin, A., Litvinov, A., Nizameev, I., Kadirov, M., Galyametdinov, Y., Antipin, I., and Konovalov, A., J. Membr. Sci., 2010, vol. 364, nos. 1–2, p. 90.
RF Patent 2362761, Byull. Izobret., 2009, no. 21.
Syakaev, V., Mustafina, A., Elistratova, Yu., Latypov, Sh., and Konovalov, A., Supramol. Chem., 2008, vol. 20, no. 5, p. 453.
Zakharova, L., Syakaev, V., Voronin, M., Valeeva, F., Ibragimova, A., Ablakova, Yu., Kazakova, E., Latypov, Sh., and Konovalov, A., J. Phys. Chem. C, 2009, vol. 113, p. 6182.
Arimori, S., Nagasaki, T., and Shinkai, S., J. Chem. Soc., Perkin Trans. 2, 1995, no. 4, p. 679.
Strobel, M., Kita-Tokarczyk, K., Taubert, A., Vebert, C., Heiney, P.A., Chami, M., and Meier, W., Adv. Funct. Mater., 2006, vol. 16, p. 252.
US Patent 4259464, 1981.
Lukashenko, S.S., Yurina, A.V., Pashirova, T.N., Kudryavtsev, D.B, Kosacheva, E.M., Kudryavtseva, L.A., and Konovalov, A.I., Kolloidn. Zh., 2008, vol. 70, no. 3, p. 351.
Kudryavtsev, D.B., Panteleeva, A.R., Yurina, A.V., Lukashenko, S.S., Khodyrev, Yu.P., Galiakberov, R.M., Khaziakhmetov, D.N., and Kudryavtseva, L.A., Pet. Chem., 2009, vol. 49, no. 3, p. 193.
Poverkhnostno-aktivnye veshchestva: Spravochnik (Handbook of Surfactants), Abramzon, A.A. and Gaevii, G.M., Eds., Leningrad: Khimiya, 1979.
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.
Kholmberg, K., Iensson, B., Kronberg, B., and Lindman, B., Poverkhnostno-aktivnye veshchestva i polimery v vodnykh rastvorakh (Surfactants and Polymers in Aqueous Solutions), Moscow: Binom, 2007.
Kudryashova, Yu.R., Valeeva, F.G., Ibragimova, A.R., Zakharova, L.Ya., and Konovalov, A.I., Kinet. Catal., 2011, vol. 52, no. 1, p. 55.
Menger, F.M. and Portnoy, C.T., J. Am. Chem. Soc., 1968, vol. 90, p. 1875.
Mirgorodskaya, A.B., Kudryavtseva, L.A., Zuev, Yu.F., and Vylegzhanina, N.N., Russ. J. Phys. Chem., 2002, vol. 76, no. 11, p. 1849.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.B. Mirgorodskaya, E.I. Yatskevich, Yu.R. Kudryashova, S.E. Solov’eva, I.S. Antipin, L.Ya. Zakharova, A.I. Konovalov, 2011, published in Kinetika i Kataliz, 2011, Vol. 52, No. 4, pp. 540–546.
Rights and permissions
About this article
Cite this article
Mirgorodskaya, A.B., Yatskevich, E.I., Kudryashova, Y.R. et al. Catalytic properties of supramolecular systems based on polyoxyethylated calixarenes and amines. Kinet Catal 52, 529–535 (2011). https://doi.org/10.1134/S0023158411040082
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158411040082