Structure and kinetics of novel cyclophane inclusion compounds

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Sylke Apel, Mátyás Czugler, Vivienne J. Griffith, Luigi R. Nassimbeni and Edwin Weber


Abstract

A novel cyclophane host compound, 3, featuring a macrocyclic structure with two hydroquinone dimethyl ether and two 1,1-diphenylcyclohexane construction elements assembled via benzylic ether linkages has been synthesised and its inclusion compounds with toluene, 4, and cyclohexanone, 5, have been characterised by thermal analysis and X-ray crystallography. The conformation of the cyclophane is markedly different in the two inclusion compounds. The kinetics of desolvation of 5 are deceleratory and yield an activation energy of 182 kJ mol–1.


References

  1. D. J. Cram, in Cyclophanes, ed. P. M. Keehn and S. M. Rosenfeld, Academic Press, New York, 1983, vol. 1 Search PubMed.
  2. D. J. Cram and J. M. Cram, Container molecules and their guests, (Monographs in Supramolecular Chemistry, Vol. 4), The Royal Society of Chemistry, Cambridge, 1994 Search PubMed.
  3. F. Diederich, Cyclophanes(Monographs in Supramolecular Chemistry, Vol. 2), The Royal Society of Chemistry, Cambridge, 1991 Search PubMed.
  4. (a) K. Odashima and K. Koga, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Elsevier, Oxford, 1996, vol. 2, p. 143 Search PubMed; (b) D. A. Dougherty, ibid., p. 195 Search PubMed.
  5. E. Weber and F. Vögtle, Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Elsevier, Oxford, 1996, vol. 2, p. 1 Search PubMed.
  6. C. Krieger and F. Diederich, Chem. Ber., 1985, 118, 3620 CAS.
  7. S. J. Abbott, A. G. M. Barrett, C. R. A. Godfrey, S. B. Kalindjian, G. W. Simpson and D. J. Williams, J. Chem. Soc., Chem. Commun., 1982, 796 RSC.
  8. K. Hirotsu, S. Kamitori, T. Higuchi, I. Tabushi, K. Yamamura and H. Nonoguchi, J. Inclusion Phenom., 1984, 2, 215 CrossRef CAS.
  9. H. Nonoguchi, K. Yamamura, I. Tabushi, T. Higuchi and K. Hirotsu, Bull. Chem. Soc. Jpn., 1992, 65, 805 CAS.
  10. K. Gloe, H. Stephan, O. Heitzsch, H. Bukowsky, E. Uhlemann, R. Pollex and E. Weber, J. Chem. Soc., Chem. Commun., 1994, 1955 RSC.
  11. C. Helbig, Ph.D. Thesis, TU-Bergakademie Freiberg, 1996.
  12. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995, 131 Search PubMed.
  13. S. Misumi, in Supramolecular Chemistry I — Directed Synthesis and Molecular Recognition(Topics in Current Chemistry, Vol. 165), ed. E. Weber, Springer-Verlag, Berlin, Heidelberg, 1993, p. 163 Search PubMed.
  14. L. R. Nassimbeni, in Crystallography of Supramolecular Compounds, ed. G. Tsoucaris, J. L. Atwood and J. Lipkowski, NATO ASI Series C, vol. 480, Kluwer Academic Publishers, Dordrecht, 1996, p. 285 Search PubMed.
  15. M. R. Caira and L. R. Nassimbeni, in Comprehensive Supramolecular Chemistry, ed. D. D. MacNicol, F. Toda and R. Bishop, Pergamon Press, 1996, vol. 6, ch. 25 Search PubMed.
  16. J. B. Niederl, V. Niederl and J. Charney, J. Am. Chem. Soc., 1940, 62, 322 CrossRef CAS.
  17. W. J. Moran, E. C. Schreiber and E. Engel, J. Am. Chem. Soc., 1952, 74, 127 CrossRef CAS.
  18. (a) A. Ostrowicki, E. Koepp and F. Vögtle, Macrocycles(Topics in Current Chemistry, Vol. 161), ed. E. Weber and F. Vögtle, Springer-Verlag, Berlin, Heidelberg, 1992, p. 37 Search PubMed; (b) J. Breitenbach, J. Boosfeld and F. Vögtle, Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Elsevier, Oxford, 1996, vol. 2, p. 29 Search PubMed.
  19. G. M. Sheldrick, SHELX-86, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  20. G. M. Sheldrick, SHELX-93. A Program for Crystal Structure Determination, unpublished results.
  21. M. R. Caira, L. R. Nassimbeni, N. Winder, E. Weber and A. Wierig, Supramol. Chem., 1994, 4, 135 CAS.
  22. K. Yvon, W. Jeitschko and E. Parthe, J. Appl. Crystallogr., 1977, 10, 73 CrossRef.
  23. A. Coetzee, Ph.D. Thesis, University of Cape Town, 1996.
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