Abstract
The complexation of a macrocycle containing thiopyrimidine and uracil moieties (M) with amino acids and some dicarboxylic acids was studied by pH-metric, UV-VIS, 1H NMR spectroscopy methods in chloroform, methanol, aqueous 1,4-dioxane, and biphasic water–chloroform media. The complexation of M with acids is too weak to solubilize them from the solid state into chloroform solutions containing M. The 1H NMR spectra and pH-metric data of aqueous 1,4-dioxane (80 vol.%) reveal the pH-dependent 1:1 binding between M and the acids studied. The protonation of M is not a prerequisite for binding of fumaric, succinic, o-phtalic acids and the series of amino acids, whereas binding of maleic acid requires the protonation of both thiopyrimidine moieties of M. Therefore,M·(H+)2 exhibits strong selectivity towards maleic acid in aqueous 1,4-dioxane and in biphasic water–chloroform media.
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References
V. Alcazar, J. R. Moran, and F. Diederich, Isr. J. Chem. 32,69 (1992).
T. Hirose, K. Naito, H. Shitara, H. Nohira, and B. W. Baldwin, Tetrahedron: Assymetry 12,375 (2001).
I. Stibor, D. S. M. Hafeed, P. Lhotak, J. Hodacova, J. Koca, and M. Cajan, Gazz. Chim. Ital. 127,673 (1997).
U. Lucking, D. M. Rudkevich, and J. Rebek Jr., Tetrahedron Lett. 41,9547 (2000).
P. Lustenberg, R. Welti, and F. Diederich, Helv. Chim. Acta 81,2190 (1998).
F. Werner and H. J. Schneider, Helv. Chim. Acta 83,465 (2000).
R. W. Hoffmann, F. Hettche, and K. Harms, Chem. Commun. 782 (2002).
A. Bencini, M. A. Bernardo, A. Bianchi, V. Fusi, C. Giorgi, F. Pina, and B. Valtancoli, Eur. J. Inorg. Chem. 1911 (1999).
Yo. Shi and H.-J. Schneider, J. Chem. Soc., Perkin Trans. 2,1797 (1999).
C. Bazzicalupi, A. Beconcini, A. Bencini, V. Fusi, C. Giorgi, A. Masotti, and B. Valtancoli, J. Chem. Soc., Perkin Trans. 2,1675 (1999).
T. Mizutani, K. Wada, and S. Kitagawa, J. Am. Chem. Soc. 121,11425 (1999).
J. L. Sessler, A. Andrievsky, V. Kral, and V. Lynch, J. Am. Chem. Soc. 119,9385 (1997).
A. De Robertis, C. De Stefano, C. Foti, O. Giuffre, and S. Sammartano, Talanta 54,1135 (2001).
L. S. Kuznetsova, A. R. Mustafina, A. S. Michailov, V. E. Kataev, and V. S. Reznik, J. Solution Chem. 31,895 (2002).
A. J. Gordon and R. A. Ford, The Chemist’s Companion. A Handbook of Practical Data, Techniques and References (Wiley-Interscience, 1972, 542 p.).
F. Jordan, J. Phys. Chem. 77,2681 (1973).
M. Sirish and H.-J. Schneider, Chem. Commun. 23 (2000).
Yu. I. Sal’nicov, F. V. Devyatov, N. E. Zhuravleva, and D. V. Golodnitskaya, Zh. Neorg. Khim. 29,2273 (1984) [J. Inorg. Chem. USSR (Trans.) 29, 1299 (1984)].
F. Rived, I. Canals, E. Bosch, and M. Roses, Anal. Chim. Acta 439,315 (2001).
J. L. Sessler and J. M. Davis, Acc. Chem. Res. 34,989 (2001).
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Mustafina, A.R., Kuznetsova, L.S., Michailov, A.S. et al. Complexation of a Macrocycle Containing Thiopyrimidine and Uracil Moieties with Dicarboxylic and Amino Acids in Various Organic and Aqueous Organic Solutions. J Solution Chem 33, 1257–1276 (2004). https://doi.org/10.1007/s10953-004-7139-x
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DOI: https://doi.org/10.1007/s10953-004-7139-x