Abstract
The stability constants of complexes of 12-, 15-, and 18-membered diaza crown ethers, N,N′-dimethyl diaza crown ethers, and N,N′-bis(2-hydroxyethyl) diaza crown ethers with alkali and alkaline-earth metal ions in 95% aqueous methanol at 25°C were determined. The stability of the complexes of unsubstituted diaza crown ethers with alkali metal cations is low, probably because of stabilization of the exo,exo conformation of the ligands due to interaction of the nitrogen lone electron pairs with the solvent. The complexes with the double-charged cations are appreciably more stable. N,N′-Dimethyl diaza crown ethers form stable complexes with all the ions studied. As compared to the dimethyl derivatives, N,N′-bis(2-hydroxyethyl) diaza crown ethers form more stable complexes with the Na+, K+, Ca2+, Sr2+, and Ba2+ ions, which is due to participation of the side hydroxyethyl groups in the coordination.
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REFERENCES
Bradshaw, J.S. and Izatt, R.M., Acc. Chem. Res., 1997, vol. 30, no.8, p. 338.
Barbour, L.J., De Wall, S.L., Meadows, E.S., and Gokel, G.W., Ind. Eng. Chem. Res., 2000, vol. 39, no.10, p. 3436.
Lukyanenko, N.G., Pastushok, V.N., Bordunov, A.V., Vetrogon, V.I., Vetrogon, N.I., and Bradshaw, J.S., J. Chem. Soc., Perkin Trans. 1, 1994, no. 11, p. 1489.
Katritzky, A.R., Denisko, O.V., and Belyakov, S.A., J. Org. Chem., 1996, vol. 61, no.21, p. 7578.
Platas, C., Avecilla, F., Blas, A., Rodriguez-Blas, T., Bastida, R., Macias, A., Rodriguez, A., and Adams, H., J. Chem. Soc., Dalton Trans., 2001, no. 11, p. 1699.
Schultz, R.A., White, B.D., Dishong, D.M., Arnold, K.A., and Gokel, G.W., J. Am. Chem. Soc., 1985, vol. 107, no.23, p. 6659.
Arnold, K.A., Echegoyen, L., Fronczek, F.R., Gandour, R.D., Gatto, V.J., White, B.D., and Gokel, G.W., J. Am. Chem. Soc., 1987, vol. 109, no.12, p. 3716.
Kilic, Z., Yildiz, M., Hoekelek, T., and Erdogan, B., J. Chem. Soc., Dalton Trans., 1998, no. 21, p. 3635.
Walters, K.M., Buntine, M.A., Lincoln, S.F., and Wainwright, K.P., J. Chem. Soc., Dalton Trans., 2002, no. 18, p. 3571.
Izatt, R.M., Bradshaw, J.S., Nielsen, S.A., Lamb, J.D., Christensen, J.J., and Sen, D., Chem. Rev., 1985, vol. 85, no.4, p. 271.
Pilichowski, J.F., Lehn, J.-M., Sauvage, J.P., and Gramain, J.C., Tetrahedron, 1985, vol. 41, no.10, p. 1959.
Bradshaw, J.S., Krakowiak, K.E., and Izatt, R.M., Aza-Crown Macrocycles, New York: Wiley, 1993.
Diettrich, B., Lehn, J.-M., Sauvage, J.P., and Blanzat, J., Tetrahedron, 1973, vol. 29, no.9, p. 1629.
D’Aprano, A. and Sesta, B., J. Solution Chem., 1988, vol. 17, no.2, p. 117.
Buschmann, H.-J., J. Solution Chem., 1986, vol. 15, no.6, p. 453.
Lukyanenko, N.G., Basok, S.S., and Filonova, L.K., J. Chem. Soc., Perkin Trans. 1, 1988, no. 12, p. 3141.
Gokel, G.W. and Korzeniowski, S.H., Macrocyclic Polyether Syntheses, Berlin: Springer, 1982, p. 156.
Wickstrom, T., Dale, J., and Lund, W., Anal. Chim. Acta, 1988, vol. 211, nos.1/2, p. 223.
Vetrogon, V.I., Lukyanenko, N.G., and Schwing-Weill, M.-J., Talanta, 1994, vol. 41, no.12, p. 2105.
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 665–669.
Original Russian Text Copyright © 2005 by Kulygina, Vetrogon, Basok, Luk’yanenko.
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Kulygina, E.Y., Vetrogon, V.I., Basok, S.S. et al. Synthesis and Complexing Properties of N,N′-Bis(2-hydroxyethyl) Diaza Crown Ethers. Russ J Gen Chem 75, 628–631 (2005). https://doi.org/10.1007/s11176-005-0284-0
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DOI: https://doi.org/10.1007/s11176-005-0284-0