The nucleophilic reactivity of HO– and HOO– ions in the presence of imidazole gemini surfactants toward 4-nitrophenyl diethyl phosphate (NPDEP) was studied. It was shown that in the micelles of these detergents, as in water, an α effect is realized for the hydroperoxide ion. Its magnitude, characterized by the ratio of the second-order rate constants k 2(HOO-) m/k 2(HO-) m for the reaction with NPDEP in the micellar pseudophase, reaches ~100. Comparable micellar effects are observed at concentrations of the gemini surfactants not less than an order of magnitude lower than in the case of their monomeric analogs.
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Notes
The CMC values were determined from the k obs–C0 relationships (Fig. 2c,d).
References
R. Zana and J. Xia (eds.), Gemini Surfactants: Synthesis, Interfacial and Solution-Phase Behavior, and Applications, Marcel Dekker Inc., New York, Basel (2004).
P. Wasserscheid and T. Welton (eds.), Ionic Liquids in Synthesis, Wiley-VCH Verlag, GmbH&Co. KGaA, Weinheim (2008).
D. Kuang, T. Brezesinski, and B. Smarsly, J. Am. Chem. Soc., 126, No. 34, 10534–10535 (2004).
S. Bhattacharya and V. P. Kumar, Langmuir, 21, No. 1, 71–78 (2005).
S. Bhattacharya and V. P. Kumar, J. Org. Chem., 69, No. 2, 559–562 (2004).
L. M. Kustov and I. P. Beletskaya, Ros. Khim. Zh. (Zh. Ros. Khim. Obshch. im. D. I. Mendeleeva), 48, No. 6, 3–12 (2004).
A. F. Popov, Pure Appl. Chem., 80, No. 7, 1381–1397 (2008).
Yu. S. Simanenko, A. F. Popov, T. M. Prokop’eva, et al., Russ. J. Org. Chem., 38, No. 9, 1286–1298 (2002).
T. N. Solomoichenko, Yu. S. Sadovskii, T. M. Prokop’eva, et al., Teor. Éksp. Khim., 42, No. 6, 357–363 (2006). [Theor. Exp. Chem., 42, No. 6, 364-370 (2006) (English translation).]
M. Chiarini, N. D. Gillitt, and C. A. Bunton, Langmuir, 18, No. 10, 3836–3842 (2002).
Yu. S. Simanenko, A. F. Popov, T. M. Prokop’eva, et al., Teor. Éksp. Khim., 38, No. 4, 238–244 (2002). [Theor. Exp. Chem., 38, No. 4, 242–249 (2002) (English translation).]
K. Martinek, A. K. Yatsimirski, A. P. Osipov, and I. V. Berezin, Tetrahedron, 29, No. 7, 963–969 (1973).
C. H. De Puy, E. W. Della, J. Filley, et al., J. Am. Chem. Soc., 105, No. 8, 2481–2482 (1983).
M. Ao, P. Huang, G. Xu, et al., Colloid Polym. Sci., 287, No. 4, 395–402 (2009).
M. Ao, G. Xu, Y. Zhu, and Y. Bai, J. Colloid Interface Sci., 326, No. 2, 490–495 (2008).
S. D. Wettig, P. Nowak, and R. E. Verrall, Langmuir, 18, No. 14, 5354–5359 (2002).
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Translated from Teoreticheskaya i Éksperimental’naya Khimiya, Vol. 48, No. 2, pp. 112-118, March-April, 2012.
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Sadovskii, Y.S., Solomoichenko, T.N., Turovskaya, M.K. et al. Peroxyhydrolysis of 4-nitrophenyl diethyl phosphate in micellar systems based on imidazolium gemini surfactants. Theor Exp Chem 48, 122–128 (2012). https://doi.org/10.1007/s11237-012-9249-7
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DOI: https://doi.org/10.1007/s11237-012-9249-7