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Catalytic properties of supramolecular systems based on polyoxyethylated calixarenes and amines

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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.

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References

  1. Fendler, J.H., Chem. Rev., 1987, vol. 87, no. 5, p. 877.

    Article  CAS  Google Scholar 

  2. Chang, G.G., Huang, T.M., and Hung, H.C., Proc. Natl. Sci. Counc. Repub. China B, 2000, vol. 24, no. 3, p. 89.

    CAS  Google Scholar 

  3. 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.

    Article  CAS  Google Scholar 

  4. Berezin, I.V., Martinek, K., and Yatsimirskii, A.K., Usp. Khim., 1973, vol. 42, no. 10, p. 1729.

    CAS  Google Scholar 

  5. Bunton, C.A. and Savelli, G., Adv. Phys. Org. Chem., 1986, vol. 22, p. 213.

    Article  CAS  Google Scholar 

  6. Micellization, Solubilization, and Microemulsion, Mittel, K., Ed., New York: Plenum, 1977.

    Google Scholar 

  7. Dwars, T., Paetzold, E., and Oehme, G., Angew. Chem. Int. Ed., 2005, vol. 44, p. 7174.

    Article  CAS  Google Scholar 

  8. Khan, M.N., Micellar Catalysis, New York: CRC, 2006.

    Book  Google Scholar 

  9. 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.

    Chapter  Google Scholar 

  10. 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.

    Article  CAS  Google Scholar 

  11. 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.

    Article  CAS  Google Scholar 

  12. RF Patent 2362761, Byull. Izobret., 2009, no. 21.

  13. Syakaev, V., Mustafina, A., Elistratova, Yu., Latypov, Sh., and Konovalov, A., Supramol. Chem., 2008, vol. 20, no. 5, p. 453.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. Arimori, S., Nagasaki, T., and Shinkai, S., J. Chem. Soc., Perkin Trans. 2, 1995, no. 4, p. 679.

  16. 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.

    Article  CAS  Google Scholar 

  17. US Patent 4259464, 1981.

  18. 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.

    Google Scholar 

  19. 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.

    Article  Google Scholar 

  20. Poverkhnostno-aktivnye veshchestva: Spravochnik (Handbook of Surfactants), Abramzon, A.A. and Gaevii, G.M., Eds., Leningrad: Khimiya, 1979.

    Google Scholar 

  21. 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.

  22. 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.

    Google Scholar 

  23. 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.

    Article  CAS  Google Scholar 

  24. Menger, F.M. and Portnoy, C.T., J. Am. Chem. Soc., 1968, vol. 90, p. 1875.

    Article  CAS  Google Scholar 

  25. Mirgorodskaya, A.B., Kudryavtseva, L.A., Zuev, Yu.F., and Vylegzhanina, N.N., Russ. J. Phys. Chem., 2002, vol. 76, no. 11, p. 1849.

    Google Scholar 

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Correspondence to A. B. Mirgorodskaya.

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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.

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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

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  • DOI: https://doi.org/10.1134/S0023158411040082

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