Abstract
The pK a values and constants of tautomeric equilibrium of several o-aminomethylphenols with different hydrophilic-lipophilic ability were measured in aqueous micellar solutions and in direct microemulsions based on cetyltrimethylammonium bromide. The kinetics of hydrolysis of p-nitrophenyl acetate at different pH and concentrations of aminomethylphenol and surfactant was studied.
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I. V. Berezin, K. Martinek, and A. K. Yatsimirskii, Usp. Khim., 1973, 42, 1729 [Russ. Chem. Rev., 1973, 42, 1343 (Engl. Transl.)].
K. Holmberg, Current Opinion in Colloid Interface Sci., 2003, 8, 187.
D. M. Vriezema, M. C. Aragones, J. A. A. W. Elemans, J. L. M. Cornelisstn, A. E. Rowan, and R. J. M. Nolte, Chem. Rev., 2005, 105, 1445.
K. K. Ghosh, D. Sinha, M. L. Satnami, D. K. Dubey, P. Rodriguez-Dafonte, and G. L. Mundhra, Langmuir, 2005, 21, 8664.
K. M. Solntsev, S. A. Al-Ainain, Y. V. Il’ichev, and M. G. Kuzmin, J. Phys. Chem., A, 2004, 108, 8212.
M. Arias, L. Garcia-Rio, J. S. Mejuto, P. Rodriguez-Dafonte, and J. Simal-Gandara, J. Agric. Food. Chem., 2005, 53, 7172.
R. A. Shagidullina, I. S. Ryzhkina, A. B. Mirgorodskaya, L. A. Kudryavtseva, and V. E. Bel’skii, Izv. Akad. Nauk SSSR, Ser. Khim., 1994, 1215 [Russ. Chem. Bull., 1994, 43, 1149 (Engl. Transl.)].
A. B. Teitel’baum, I. S. Ryzhkina, L. A. Kudryavtseva, V. E. Bel’skii, and B. E. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 1016 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 32, 918 (Engl. Transl.)].
B. Reichert, Die Mannich Reaction, Springer Verlag, Berlin-Gottingen-Heidelberg, 1959, 192.
L. Ya. Zakharova, F. G. Valeeva, A. V. Zakharov, A. R. Ibragimova, L. A. Kudryavtseva, and H. E. Harlampidi, J. Colloid Interface Sci., 2003, 263, 597.
A. B. Mirgorodskaya, L. A. Kudryavtseva, L. Ya. Zakharova, and V. E. Bel’skii, Izv. Akad. Nauk, Ser. Khim., 1998, 1333 [Russ. Chem. Bull., 1998, 47, 1296 (Engl. Transl.)].
A. B. Mirgorodskaya and L. A. Kudryavtseva, Zh. Obshch. Khim., 2002, 72, 1343 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
R. A. Mackay and C. Hermansky, J. Phys. Chem., 1981, 85, 739.
A. B. Teitel’baum, K. A. Derstuganova, N. A. Shishkina, L. A. Kudryavtseva, V. E. Bel’skii, and B. E. Ivanov, Izv. Akad. Nauk SSSR. Ser. Khim., 1980, 803 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, 29, 558 (Engl. Transl.)].
A. B. Teitel’baum, L. A. Kudryavtseva, V. E. Bel’skii, and B. E. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 2253 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, 29, 1571 (Engl. Transl.)].
I. S. Ryzhkina, L. A. Kudryavtseva, K. M. Enikeev, V. I. Morozov, G. A. Boss, and Yu. I. Sal’nikov, Izv. Akad. Nauk, Ser. Khim., 2000, 1355 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1349].
R. A. Shagidullina, L. A. Kudryavtseva, A. B. Mirgorodskaya, L. Ya. Zakharova, and B. E. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1126 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1010 (Engl. Transl.)].
J. F. Kirsh and W. P. Jencks, J. Am. Chem. Soc., 1964, 86, 837.
E. J. Fendler and J. H. Fendler, Adv. Phys. Org. Chem., 1970, 8, 271.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1724–1729, October, 2006
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Mirgorodskaya, A.B., Erzikova, N.S., Kudryavtseva, L.A. et al. Acid-base properties and nucleophilicity of o-aminomethylphenols in aqueous micellar solutions and microemulsions. Russ Chem Bull 55, 1788–1793 (2006). https://doi.org/10.1007/s11172-006-0488-4
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DOI: https://doi.org/10.1007/s11172-006-0488-4