Abstract
The drug homologue, 5-aminothiabendazole, contains four major centers of basicity, and is an excellent sensor of the microenvironment in AOT reversed micelles at varying levels of added water. Its parent drug, thiabendazole, is an anthelmintic/antimalarial agent widely used in animals, and as a fungicide on fruits and vegetables. The 5-amino derivative’s absorption and fluorescence spectra are unusually sensitive to pH, polarity, viscosity, and complexation effects. Spectral data strongly indicates three types of solubilization sites in AOT medium. At low R values, where R is the water to surfactant molar ratio, ground state absorbance spectra indicate that the lone pair of electrons on the amino group is strongly hydrogen bonded by the highly interactive water present in the core. An unbound form in a methanol-type environment is also in evidence. As the amount of water is increased, the extent of hydrogen bonding of the amino substituent decreases, and more probe appears unbound in the enlarging water pool. Fluorescence spectral data reflect excited state protonation of the unbound free base form occurring, which does not occur in ordinary bulk water, and it becomes more extensive as the water core increases in size. This is likely due to the still atypical structure of water in the 0.13 to 12 R value range studied, and the micellar core water’s enhancement effects on the kinetics of prototropic reactions.
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References
H. F. Eicke, Top. Curr. Chem., 87, 86 (1980).
J. H. Fendler, Acc. Chem. Res., 9, 153 (1976).
F. M. Menger and K. Yamada, J. Am. Chem. Soc., 101, 6731 (1979).
S. Barbaric and P. L. Luisi, J. Am. Chem. Soc., 103, 4239 (1981).
O. A. El Seoud and M. J. Silva, J. Chem. Soc., Perkin II, 76, 127 (1980).
E. Bardez, B. T. Goguillon, E. Keh and B. Valeur, J. Phys. Chem., 88, 1909 (1984).
M. Wong, J. K. Thomas and M. Gratzel, J. Am. Chem. Soc., 98, 2391 (1976).
E. Keh and B. Valeur, J. Colloid Interface Sci., 79, 4654 (1981).
H. Kondo, I. Miwa and J. Sunamoto, J. Phys. Chem., 86, 4826 (1982).
R. A. Day and B. H. Robinson, J. Chem. Soc., 75, 132 (1979).
M. Wong, J. K. Thomas and T. Nowak, J. Am. Chem. Soc., 99, 4730 (1977).
V. Calvo-Perez, G. Beddard and J. H. Fendler, J. Phys. Chem., 85, 2316 (1981).
P. C. Tway and L. J. Cline Love, J. Phys. Chem., 86, 5227 (1982).
P. C. Tway and L. J. Cline Love, J. Phys. Chem., 86, 5223 (1982).
R. E. Smith and P. L. Luisi, Helv. Chim. Acta, 63, 2302 (1980).
O. A. El Seoud and A. M. Chinelatto, J. Colloid Interface Sci., 95, 163 (1983).
F. M. Menger and G. Saito, J. Am. Chem. Soc., 100, 4376 (1978).
L. J. Magid, K. Konno and C. A. Martin, J. Phys. Chem., 85, 1434 (1981).
K. Tamura and Z. A. Schelly, J. Am. Chem. Soc., 103, 1018 (1981).
S. G. Schulman and A. C. Capomacchia, Anal. Chim. Acta, 58, 91 (1972).
S. G. Schulman, in “Physical Methods in Heterocyclic Chemistry”, Vol. VI, A. R. Katritzky, Ed., pp. 147–97, Academic Press, New York, 1974.
F. M. Menger, G. Saito, G. V. Sanzero and J. R. Dodd, J. Am. Chem. Soc., 97, 909 (1975).
M. Zulauf and H. F. Eicke, J. Phys. Chem., 83, 480 (1979).
J. H. Fendler, J. Am. Chem. Soc., 100, 2234 (1978).
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Love, L.J.C., Noroski, J.E. (1986). Effects of Reversed Micelles on Prototropic Interactions and Fluorescence Behavior of 5-Aminothiabendazole: a Model Bioaggregates System for Drugs. In: Mittal, K.L., Bothorel, P. (eds) Surfactants in Solution. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-7981-6_8
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DOI: https://doi.org/10.1007/978-1-4615-7981-6_8
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