Solvation of Calix[4]arene-bis-crown-6 Molecules

  • Jeffrey C. Bryan
  • Tianniu Chen
  • Tatiana G. Levitskaia
  • Tamara J. Haverlock
  • Craig E. Barnes
  • Bruce A. Moyer
Article

Abstract

Single crystal X-ray diffraction analyses of calix[4]arene-bis-crown-6 (1) and calix[4]arene-bis-benzocrown-6⋯1,2-dichloroethane (2) are reported. Thesestructures offer an opportunity to study the conformation of calix[4]arene-bis-crown-6 molecules in the absence of solvent, and when very weakly solvated. These structures exhibit different conformations of the crown ring, and limited flexibility of the calix[4]arene,but do not show solvent or crown inclusion in the calix[4]arene cavity. Comparisons to similar structures are made, and the implications for cesium binding are discussed.

crown ether solvation calixarene crystal structure 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    B.A. Moyer: In G.W. Gokel (ed.), Complexation and Transport (Comprehensive Supramolecular Chemistry v. 1, Pergamon (1996), pp. 377–416.Google Scholar
  2. 2.
    B.A. Moyer and P.V. Bonnesen: In A. Bianchi, K. Bowman-James, and E. Garcia-Espana (eds.), Physical Factors in Anion Separations (Supramolecular Chemistry of Anions), Wiley-VCH (1997), pp. 1–42.Google Scholar
  3. 3.
    K. Kavallieratos, A.M. Danby, G.J. Van Berkel, M.A. Kelly, R.A. Sachleben, B.A. Moyer, and K. Bowman-James: Anal. Chem. 72, 5258 (2000).Google Scholar
  4. 4.
    K. Kavallieratos, R.A. Sachleben, G.J. Van Berkel, and B.A. Moyer: J. Chem. Soc., Chem. Commun. 187 (2000).Google Scholar
  5. 5.
    B.A. Moyer, P.V. Bonnesen, C.K. Chambliss, T.J. Haverlock, A.P. Marchand, H-S. Chong, A.S. McKim, K. Krishnudu, K.S. Ravikumar, V.S. Kumar, and M. Takhi: In P.G. Eller and W.R. Heineman (eds.), Use of Cage-Functionalized Macrocycles and Fluorinated Alcohols in the Liquid- Liquid Extraction of NaOH and other Sodium Salts: Strategies Toward Waste-Volume Reduction (Nuclear Site Remediation: First Accomplishments of the Environmental Science Program, ACS Symposium Series, v. 778, American Chemical Society (2001), pp. 114–132.Google Scholar
  6. 6.
    D.J. Cram: Angew. Chem. 98, 1041 (1986).Google Scholar
  7. 7.
    R.A. Sachleben, P.V. Bonnesen, T. Descazeaud, T.J. Haverlock, A. Urvoas, and B.A. Moyer: Solvent Extr. Ion Exch. 17, 1445 (1999).Google Scholar
  8. 8.
    V. Lamare, J.-F. Dozol, S. Fuangswasdi, F. Arnaud-Neu, P. Thuéry, M. Nierlich, Z. Asfari, and J. Vicens: J. Chem. Soc., Perkin Trans. 2 271 (1999).Google Scholar
  9. 9.
    F. Arnaud-Neu, Z. Asfari, B. Souley, and J. Vicens: New J. Chem. 20, 453 (1996).Google Scholar
  10. 10.
    G. Wipff and M. Lauterbach: Supramol. Chem. 6, 187 (1995).Google Scholar
  11. 11.
    P. Thuéry, M. Nierlich, J.C. Bryan, V. Lamare, J.-F. Dozol, Z. Asfari, and J. Vicens: J. Chem. Soc., Dalton Trans. 4191 (1997).Google Scholar
  12. 12.
    P. Thuéry, M. Nierlich, V. Lamare, J.-F. Dozol, Z. Asfari, and J. Vicens: J. Incl. Phenom. Mol. Recognit. Chem. 36, 375 (2000).Google Scholar
  13. 13.
    T.J. Haverlock, P.V. Bonnesen, R.A. Sachleben, and B.A. Moyer: J. Incl. Phenom. Macro. Chem. 36, 21 (2000).Google Scholar
  14. 14.
    P. Lhoták and S. Shinkai: J. Phys. Org. Chem. 10, 273 (1997).Google Scholar
  15. 15.
    A. Varnek and G. Wipff: J. Mol. Struct. 363, 67 (1996).Google Scholar
  16. 16.
    Z. Asfari, C. Naumann, J. Vicens, M. Nielich, P. Thuéry, C. Bressot, V. Lamare, and J.-F. Dozol: New J. Chem. 20, 1183 (1996).Google Scholar
  17. 17.
    P. Thuéry, M. Nierlich, Z. Asfari, J. Vicens, and J.-F. Dozol: Polyhedron 19, 1749 (2000).Google Scholar
  18. 18.
    J.C. Bryan, A.P. Marchand, and A. Hazlewood: Acta Crystallogr. E 57, 13 (2001), and references therein.Google Scholar
  19. 19.
    SAINT (Version 5.00), Bruker AXS Inc., Madison, Wisconsin USA (1998).Google Scholar
  20. 20.
    G.M. Sheldrick: SADABS, A Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen, Göttingen, Germany (1996).Google Scholar
  21. 21.
    SHELXTL (Version 5.1, IRIX), Bruker Analytical X-ray Instruments, Madison, Wisconsin, USA (1997).Google Scholar
  22. 22.
    A.L. Spek: PLATON: A Multi-Purpose Crystallographic Tool, Universiteit Utrecht, The Netherlands (2001).Google Scholar
  23. 23.
    H.D. Flack: Acta Crystallogr. A39, 876 (1983).Google Scholar
  24. 24.
    F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor: J. Chem. Soc., Perkin Trans. 2 S1 (1987).Google Scholar
  25. 25.
    T. Steiner: Crystallogr. Rev. 6, 1 (1996).Google Scholar
  26. 26.
    J. Dale: Isr. J. Chem. 20, 3 (1980).Google Scholar
  27. 27.
    V. Böhmer: Angew. Chem. 107, 785 (1995).Google Scholar
  28. 28.
    P. Thuéry, M. Nierlich, Z. Asfari, and J. Vicens: J. Incl. Phenom. 27, 169 (1997).Google Scholar
  29. 29.
    R.A. Sachleben, A. Urvoas, J.C. Bryan, T. J. Haverlock, B.P. Hay, and B.A. Moyer: J. Chem. Soc., Chem. Commun. 1751 (1999).Google Scholar

Copyright information

© Kluwer Academic Publishers 2002

Authors and Affiliations

  • Jeffrey C. Bryan
    • 1
  • Tianniu Chen
    • 2
  • Tatiana G. Levitskaia
    • 1
  • Tamara J. Haverlock
    • 1
  • Craig E. Barnes
    • 2
  • Bruce A. Moyer
    • 1
  1. 1.Oak Ridge National LaboratoryChemical and Analytical Sciences DivisionOak RidgeUSA
  2. 2.Department of ChemistryThe University of TennesseeKnoxvilleUSA

Personalised recommendations