Abstract
New phosphorylated calix[4]resorcinarene and cavitands were synthesized. Their extraction ability toward LaIII, GdIII, and YbIII ions was studied. The cavitands are more efficient extracting agents than octasubstituted calix[4]resorcinarenes. The nature of substituents at the nitrogen atom at the upper rim and hydrophobic substituents at the lower rim exerts a substantial effect on the solubility of the extracted complex in chloroform. Coordination of two lanthanide ions with an extragent molecule results in their efficient but non-selective extraction. The literature and our spectral (31P NMR) data suggested that the ligand in the extracted complex has most probably a “kite” conformation.
Similar content being viewed by others
References
Y. Marcus and A. S. Kertes, Ion Exchange and Solvent Extraction of Metal Complexes, J. Wiley, London, 1969, 1/1050, 432.
N. A. Kostromina, Kompleksonaty redkozemel’nykh elementov [Rare-Earth Element Complexonates], Nauka, Moscow, 1980, 219 pp. (in Russian).
V. Alexander, Chem. Rev., 1995, 95, 273.
F. Arnaud-Neu, Chem. Soc. Rev., 1994, 23, 235.
I. M. Harrowfield, M. Mocerino, B. J. Peachey, B. W. Skelton, and A. H. White, J. Chem. Soc., Dalton Trans., 1996, 1687.
L. Atamas, O. Klimchuk, V. Rudzevich, V. Pirozhenko, V. Kalchenko, I. Smirnov, V. Babain, T. Efremova, A. Varnek, G. Wipff, F. Arnaud-Neu, M. Roch, M. Saadioui, and V. Böhmer, J. Supramol. Chem., 2002, 2, 421.
J. F. Malone, D. J. Marrs, M. A. McKervey, P. O’Hagan, N. Thompson, A. Walker, F. Arnaud-Neu, O. Naupriver, M. R. Schwing-Weill, J. F. Dozol, H. Rouquette, and N. Simon, J. Chem. Soc., Chem. Commun., 1995, 2151.
M. R. Schwing-Weill and F. Arnaud-Neu, Gazz. Chim. Ital., 1997, 127, 687.
F. Arnaud-Neu, V. Böhmer, J. F. Dozol, C. Grüttner, R. A. Jacobi, D. Kraft, O. Mauprivez, H. Rouquette, M. R. Schwing-Weill, N. Simon, and W. Vogt, J. Chem. Soc., Perkin Trans. 2, 1996, 1175.
S. Barboso, A. C. Carrera, S. E. Matthews, F. Arnaud-Neu, V. Böhmer, J. F. Dozol, H. Rouquette, and M. R. Schwing-Weill, J. Chem. Soc., Perkin Trans. 2, 1999, 719.
T. Lambert, G. D. Jarvinen, and A. S. Gopalan, Tetrahedron Lett., 1999, 40, 1613.
H. Boerrigter, W. Verboom, and D. N. Reinhoudt, J. Org. Chem., 1997, 62, 7148.
M. R. Yaftian, M. Burgard, C. Wieser, C. B. Dieleman, and D. Matt, Solv. Extr. Ion. Exch., 1998, 16, 1131.
P. D. Beer, M. G. B. Drew, and M. I. Ogden, J. Chem. Soc., Dalton Trans., 1997, 1489.
P. D. Beer, M. G. B. Drew, M. Kan, and P. B. Leeson, Inorg. Chem., 1996, 35, 2202.
P. Delange and J.-P. Dutasta, Tetrahedron Lett., 1995, 36, 9325.
P. Amrhein, P. L. Wash, A. Shivanyuk, and J. Rebek, Jr, Org. Lett., 2002, 4, 319.
A. J. Gordon and R. A. Ford, The Chemist’s Companion, Wiley, New York, 1972.
S. J. Lyle and M. M. Rahman, Talanta, 1963, 10, 1177.
K. E. Koenig, G. M. Lein, P. Stuckler, T. Kaneda, and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 3553.
R. C. Helgeson, G. R. Weisman, J. L. Toner, T. L. Tarnowski, Y. Chao, J. M. Mayer, and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 4928.
V. I. Maslennikova, O. S. Serkova, M. Gruner, S. Goutal, I. Bauer, W. D. Habicher, K. A. Lyssenko, M. Yu. Antipin, and E. E. Nifantyev, Eur. J. Org. Chem., 2004, 4884.
J. R. Fransen and Ph. J. Dutton, Can. J. Chem., 1995, 73, 221.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 303–308, February, 2007.
Rights and permissions
About this article
Cite this article
Mustafina, A.R., Zagidullina, I.Y., Maslennikova, V.I. et al. Liquid extraction of LaIII, GdIII, and YbIII ions by phosphorylated calix[4]resorcinarene derivatives. Russ Chem Bull 56, 313–319 (2007). https://doi.org/10.1007/s11172-007-0051-y
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-007-0051-y