Abstract
The amphiphilic calix[4]resorcinolarenes, aminomethylated calix[4]resorcinolarenes, o-aminomethylphenols, and their quaternary derivatives in water—dimethylformamide media (10—75 vol.% DMF) form aggregates, which catalyze the hydrolysis of phosphonous esters. The ability to self-association and the catalytic activity of the aggregates depend on the hydrophobicity of the amphiphilic compound, the pH of solution, and the content of DMF.
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I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Burilov, E. Kh. Kazakova, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 1998, 275 [Russ. Chem. Bull., 1998, 47, 269 (Engl. Transl.)].
I. S. Ryzhkina, L. A. Kudryavtseva, A. R. Mustafina, Yu. E. Morozova, E. Kh. Kazakova, K. M. Enikeev, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 1999, 456 [Russ. Chem. Bull., 1999, 48, 453 (Engl. Transl.)].
I. S. Ryzhkina, L. A. Kudryavtseva, Ya. A. Babkina, K. M. Enikeev, M. A. Pudovik, and A. I. Konovalov, Izv. Akad. Nauk, Ser. Khim., 2000, 1361 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1355].
R. Jairam, P. G. Potvin, and S. Balsky, J. Chem. Soc., Perkin Trans. 2,1999, 363.
A. D. Pidwell, S. R. Collinson, S. J. Coles, M. B. Harsthouse, M. Schroder, and D. W. Bruce, Chem. Commun., 2000, 955.
S. Arimori, T. Nagasaki, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1995, 679.
S. Shinkai, T. Arimura, K. Araki, and H. Kawabata, J. Chem. Soc., Perkin Trans. 1, 1989, 2039.
S. Shinkai, in Calixarenes, a Versalite Class of Macrocyclic Compounds, Eds. J. Vicens and V. Bohmer, Kluwer, Dordrecht, 1990, 173.
B. Reichert, Die Mannich-Reaktion, Springer-Verlag, Berlin-Göttingen-Heidelberg, 1959, 192 p.
E. P. Tishkova, L. A. Kudryavtseva, L. Ya. Zakharova, and S. B. Fedorov, Izv. Akad. Nauk, Ser. Fiz., 1996, 60, No 4, 109 [Russ. Phys. Bull., 1996, 60, No. 4 (Engl. Transl.)].
L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Wieser, J. A. Byant, J. C. Sherman, R. C. Helgeson, C. B. Knober, and D. J. Cram, J. Org. Chem., 1989, 54, 1305.
Y. Matsuskita and T. Matsui, Tetrahedron Lett., 1993, 34, 7433.
V. E. Bel´skii, L. A. Kudryavtseva, O. M. Il´ina, and B. E. Ivanov, Zh. Obshch. Khim., 1979, 49, 2470 [J. Gen. Chem., 1979, 49 (Engl. Transl.)].
Svoistva organicheskikh soedinenii. Spravochnik [Properties of Organic Compouinds. Handbook], Ed. A. A. Potekhin, Khimiya, Leningrad, 1984, 520 pp. (in Russian).
E. Fendler and J. Fendler, in Advances in Physical Organic Chemistry, Ed. V. Gold, Academic Press, London, 1970, 8.
R. A. Shagidullina, I. S. Ryzhkina, A. B. Mirgorodskaya, L. A. Kudryavtseva, V. E. Bel´skii, and B. E. Ivanov, Izv. Akad. Nauk, Ser. Khim., 1994, 1215 [Russ. Chem. Bull., 1994, 43, 1149 (Engl. Transl.)].
F. M. Menger and V. A. Migulin, J. Org. Chem., 1999, 64, 8916.
J. E. Gordon, The Organic Chemistry of Elecrtolyte Solutions, A Wiley-Interscience-J. Wiley and Sons, New York, 1975.
W. P. Jencks, Catalysis in Chemistry and Enzymology, McGrau-Hill Book Company, New York, 1969.
S. B. Sulthana, S. G. T. Bhat, and A. K. Rakshit, Bull. Chem. Soc. Jpn., 2000, 73 , 281.
A. I. Rusanov, Zh. Vsesoyuz. khim. o-va im. D. I. Mendeleeva, 1989, 174 [Mendeleev Chem. J., 1989, No. 2 (Engl. Transl.)].
A. I. Serdyuk and R. V. Kucher, Mitsellyarnye perekhody v rastvorakh poverkhnostno-aktivnykh veshchestv [Micellar Transitions in Solutions of Surfactants], Naukova Dumka, Kiev, 1987, 208 pp. (in Russian).
I. S. Ryzhkina, L. A. Kudryavtseva, K. M. Enikeev, V. I. Morozov, G. A. Boos, and Yu. I. Sal´nikov, Izv. Akad. Nauk, Ser. Khim., 2000, 1355 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1349].
E. P. Zhil´tsova, L. A. Kudryavtseva, A. P. Timosheva, N. I. Bashmakova, A. V. Chernova, and A. I. Konovalov, Elektro-khimicheskie, opticheskie i kineticheskie metody v khimii. Sbornik trudov, posvyashchennyi yubileyu professora V. F. Toropovoi [Electrochemical, Optic, and Kinetic Methods in Chemistry. Collected Reports to the Anniversary of Prof. V. F. Toropova], KGU, Kazan´, 2000, 145 pp. (in Russian).
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Ryzhkina, I.S., Babkina, Y.A., Lukashenko, S.S. et al. The aggregartion and catalytic activity of amphiphilic calix[4]resorcinolarenes and phenols in hydrolysis of phosphonous esters in water—dimethylformamide media. Russian Chemical Bulletin 51, 2183–2188 (2002). https://doi.org/10.1023/A:1022118931584
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DOI: https://doi.org/10.1023/A:1022118931584