Abstract
In combination with an ion pair extraction of potassium salts by dicyclohexyl-18-crown-6 (DC18C6), extraction behavior of anions with a diphenylthiourea (DPTU) from aqueous phase into nitrobenzene has been examined. The extraction selectivity of potassium salts follows a Hofmeister series: NO3–>Br–>Cl–>OAc–. The extractability of KCl by DC18C6 is significantly enhanced upon the addition of DPTU in organic solution. The slope analysis of the extraction equilibrium reveals a 1:1 complex formation between DPTU and Cl–. The hydrogen-bonding interaction of DPTU with Cl– is confirmed by the 1H NMR analysis in d5-nitrobenzene. For qualitative evaluation, solid-liquid extraction of KCl into d5-nitrobenzene containing DPTU and DC18C6 has been examined by 1H NMR analysis. Similar to the liquid-liquid extraction, an efficient synergistic effect of DPTU for the extraction of KCl is clarified.
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D. M. Rudkevich, Z. Brzozka, M. Palys, H. C. Visser, W. Verboom and D. N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 33, 467 (1994).
J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro and D. N. Reinhoudt, J. Org. Chem., 60, 6448 (1995).
K. I. Kinnear, D. P. Mousley, E. Arafar and J. C. Lockhart, J. Chem. Soc., Dalton Trans., 1994, 3637.
P. D. Beer, M. G. B. Drew, R. J. Knubley and M. I. Ogden, J. Chem. Soc., Dalton Trans., 1995, 3117.
P. D. Beer, F. Szemes, V. Balzani, C. M. Sala, M. G. B. Drew, S. W. Dent and M. Maestri, J. Am. Chem. Soc., 119, 11864 (1997).
J. E. Redman, P. D. Beer, S. W. Dent and M. G. B. Drew, Chem. Commun., 1998, 231
P. D. Beer and S. W. Dent, Chem. Commun., 1998, 825.
J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen and D. N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 35, 1090 (1996).
F. P. Schmidtchen and M. Berger, Chem. Rev., 97, 1609 (1997).
E. Fan, S. A. Van Arman, S. Kincaid and A. D. Hamilton, J. Am. Chem. Soc., 115, 369 (1993).
C. S. Wilcox, E.-I. Kim, D. Romano, L. H. Kuo, A. L. Burt and D. P. Curran, Tetrahedron, 51, 621 (1995).
S. Nishizawa, P. Bühlmann, K. P. Xiao and Y. Umezawa, Anal. Chim. Acta, 358, 35 (1998).
P. Bühlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron, 53, 1647 (1997).
K. P. Xiao, P. Bühlmann, S. Nishizawa, S. Amemiya and Y. Umezawa, Anal. Chem., 69, 1038 (1997).
S. Amemiya, P. Bühlmann and Y. Umezawa, Chem. Commun., 1997, 1027.
R. C. Jagessar and D. H. Burns, Chem. Commun., 1997, 1685.
S. Nishizawa, R. Kato, T. Hayashita and N. Teramae, Anal. Sci., 14, 595 (1998).
S. Nishizawa and N. Teramae, Anal. Sci., 13 (supplement), 485 (1997).
S. Nishizawa, H. Kaneda, T. Uchida and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 11, 2325 (1998).
H. C. Visser, D. M. Rudkevich, W. Verboom, F. de Jong and D. N. Reinhoudt, J. Am. Chem. Soc., 116, 11554 (1994).
E. Bakker, P. Bühlmann and E. Pretsch, Chem. Rev., 97, 3083 (1997).
P. Bühlmann, E. Bakker and E. Pretsch, Chem. Rev., 98, 1593 (1998).
C. Behringer, B. Lehmann and W. Simon, Chimia, 41, 397 (1987).
E. Wang and M. E. Meyerhoff, Anal. Chim. Acta, 283, 673 (1993).
T. Hayashita, M. Kumazawa, J. C. Lee and R. A. Bartsch, Chem. Lett., 1995, 711.
R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen and D. Sen, Chem. Rev., 85, 271 (1985).
K. A. Connors, “Binding Constants”, p. 141, John Wiley & Sons, New York, 1987.
C. S. Wilcox, in “Frontiers in Supramolecular Chemistry”, ed. H. Schneider and H. Durr, pp. 123–143, VCH, Weinheim, 1991.
D. Wegmann, H. Weiss, D. Ammann, W. E. Morf, E. Pretsch, K. Sugahara and W. Simon, Mikrochim. Acta, 3, 1 (1984)
F. Hofmeister, Arch. Exp. Pathol. Pharmakol., 24, 247 (1988).
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Murad, M.M., Hayashita, T., Shigemori, K. et al. Efficient Ion-Pair Extraction of Potassium Chloride from Aqueous Phase into Nitrobenzene Containing Dicyclohexyl-18-crown-6 as Cation Binder and Diphenylthiourea as Anion Binder. ANAL. SCI. 15, 1185–1190 (1999). https://doi.org/10.2116/analsci.15.1185
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DOI: https://doi.org/10.2116/analsci.15.1185