Complexation with diol host compounds. Part 25.1 Selective inclusion of benzenediol isomers by 1,1-bis(4-hydroxyphenyl)cyclohexane

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Mino R. Caira, Alicia Horne, Luigi R. Nassimbeni and Fumio Toda


Abstract

The title host compound includes all the isomers of the benzenediols. The structures with the p- and o-benzenediols have been elucidated and show that the clathrates are stabilised by hydrogen bonds. Competition experiments with the host in water suspension show that the para-isomer is preferentially enclathrated. Lattice energy calculations explain the results of the competition experiment.


References

  1. For Part 24, see M. R. Caira, A. Coetzee, L. R. Nassimbeni, E. Weber and A. Wierig, J. Chem. Soc., Perkin Trans. 2, 1997, 237 Search PubMed.
  2. D. J. Cram and J. M. Cram, Container Molecules and Their Guests, Royal Society of Chemistry, Cambridge, 1994 Search PubMed.
  3. F. Vögtle, Supramolecular Chemistry, Wiley, Chichester, 1991, ch. 5 Search PubMed.
  4. Inclusion Compounds, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, vol. 1–3, Academic Press, London, 1984; vol. 4 and 5, Oxford University Press, Oxford, 1991 Search PubMed.
  5. Comprehensive Supramolecular Chemistry, eds. J.-M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Pergamon Press, Oxford, 1996, vol. 1–11 Search PubMed.
  6. E. Weber, I. Csöregh, B. Stensland and M. Czugler, J. Am. Chem. Soc., 1984, 106, 3297 CrossRef CAS.
  7. F. Toda, Y. Tagami and C. W. Mak, Chem. Lett., 1986, 1909 CAS.
  8. M. R. Caira, L. R. Nassimbeni, J. L. Scott and F. Toda, J. Chem. Crystallogr., 1994, 24, 495 CAS.
  9. M. R. Caira, L. R. Nassimbeni, J. L. Scott and F. Toda, J. Chem. Crystallogr., 1994, 24, 545 CAS.
  10. S. A. Bourne, L. R. Nassimbeni and F. Toda, J. Chem. Soc., Perkin Trans. 2, 1991, 1335 RSC.
  11. S. A. Bourne, L. R. Nassimbeni, E. Weber and K. Skobridis, J. Org. Chem., 1992, 57, 2438 CrossRef CAS.
  12. D. Worsch and F. Vögtle, Topics in Current Chemistry Vol. 140, Molecular Inclusion and Molecular Recognition – Clathrates I, ed. E. Weber, Springer-Verlag, Berlin, 1987 Search PubMed.
  13. T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 383 RSC.
  14. I. Goldberg, Z. Stein, K. Tanaka and F. Toda, J. Inclusion Phenom., 1988, 6, 15 CrossRef CAS.
  15. M. R. Caira, A. Horne, L. R. Nassimbeni, K. Okuda and F. Toda, J. Chem. Soc., Perkin Trans. 2, 1995, 1063 RSC.
  16. G. M. Sheldrick, SHELX-86, Crystallographic Computing 3, eds. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford University Press, 1985 Search PubMed.
  17. G. M. Sheldrick, SHELXL-93: Programme for Crystal Structure Determination, unpublished work.
  18. W. D. S. Motherwell, in ‘EENY – Potential Energy Program’, Cambridge University, England, unpublished.
  19. C. F. Marais, ‘HEENY – Modification of EENY to allow H-bonding calculations’, University of Cape Town, 1990.
  20. E. Giglio, Nature, 1969, 222, 339 CAS.
  21. A. J. Pertsin and A. I. Kitaigorodsky, The Atom–Atom Potential Method, Chemical Physics 43, Springer-Verlag, Berlin, 1987, ch. 3 Search PubMed.
  22. A. Vedani and J. D. Dunitz, J. Am. Chem. Soc., 1985, 107, 7653 CrossRef CAS.
  23. S. A. Bourne, L. Johnson, C. Marais, L. R. Nassimbeni, E. Weber, K. Skobridis and F. Toda, J. Chem. Soc., Perkin Trans. 2, 1991, 1707 RSC.
  24. A. Gavezzotti, Structure Correlation, eds. H.-B. Bürgi and J. D. Dunitz, VCH, New York, vol. 2, ch. 12 Search PubMed.
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