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Journal of Structural Chemistry

, Volume 40, Issue 5, pp 705–713 | Cite as

4-(2,4-dihydroxyphenyl)-2,2,4-trimethylchroman: A diol counterpart of Dianin’s compound

  • T. W. Beresford
  • C. S. Frampton
  • J. H. Gall
  • D. D. MacNicol
Article

Abstract

The title resorcinol forms true clathrates analogous to those formed by Dianin’s compound itself; the ethyl acetate clathrate has space group R3, with a = 27.222(3), c = 10.727(2) å, and Z = 18 (host). One of the diol host’s OH groups participates in a hydrogen-bonded [OH]6 unit, whilst the other forms an 0H...0 (ether) hydrogen bond to an adjacent hexameric unit stacked (infinitely) along the c axis. In contrast to Dianin’s compound, sublimation in vacuo does not give the stable “empty” cage form, but leads to spontaneous resolution, the unsolvated crystal being orthorhombic, space group P212121 with a = 9.9031(15), b = 10.599(3), c= 13.501(4) Å, and Z = 4. Molecules are now linked head- to- tail by OH...0 (ether) hydrogen bonds to form infinite chains translationally propagated along a. Two such adjacent, parallel chains, related by a 21 screw axis along a, form a pair consolidated by intemwlecular hydrogen bonds of OH...O(H) type, involving both hydroxyl groups of the diol.

Keywords

Clathrate EtOAc Inclusion Compound Screw Axis Dimethyl Acetylenedicarboxylate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    A. P. Dianin,J. Russ. Phys. Chem. Soc,46, 1310 (1914).Google Scholar
  2. 2.
    For a recent review see, e.g., P. Finocchiaro and S. Failla in:Comprehensive Supramolecular Chemistry, Vol. 6, D. D. MacNicol, F. Toda, and R. Bishop (eds.), Pergamon, Oxford (1996), Ch. 18, pp. 618–627.Google Scholar
  3. 3.
    See, e.g., W. Baker, A. J. Floyd, J. F. W. McOmie, et al.,J. Chem. Soc, 2010 (1956).Google Scholar
  4. 4.
    J. L. Flippen, J. Karle, and I. L. Karle,J. Am. Chem. Soc,92, 3749 (1970); J. L. Flippen and J. Karle,J. Phys. Chem.,75, 3566(1971).CrossRefGoogle Scholar
  5. 5.
    J. A. Ripmeester,J. Incl. Phenom.,1, 87 (1983); see also, E. Zaborowski and S. Vega,Mol. Phys., 78, 703 (1993) (2H NMR, and energy calculations).CrossRefGoogle Scholar
  6. 6.
    A. A. McConnell, D. D. MacNicol, and A. L. Porte,J. Chem. Soc. (A), 3516 (1971).Google Scholar
  7. 7.
    F. Imashiro,J. Am. Chem. Soc,115, 2231 (1993).CrossRefGoogle Scholar
  8. 8.
    M. Zakrzewski and M. A. White,Condens. Matter News,2,1 [Chem. Abstr.,118, 233, 157b (1993)].Google Scholar
  9. 9.
    M. Davies and K. Williams,Trans. Faraday Soc,64, 529 (1968); J. S. Cook, R. G. Heydon, and H. K. Welsh,J. Chem. Soc. Faraday II, 1591 (1974); P. Dansas and P. Sixou,Mol. Phys.,31, 1319 (1976).CrossRefGoogle Scholar
  10. 10.
    P. C. Goswami, P. de Mayo, N. Ramnath, et al..Can. J. Chem.,63, 2719 (1985).CrossRefGoogle Scholar
  11. 11.
    See, e.g., D. D. MacNicol in:Inclusion Compounds, Vol. 2, J. L. Atwood, J. E. D. Davies, and D. D. MacNicol (eds.), Academic Press, London (1984), Ch. 1, pp. 12–29; D. D. MacNicol, J. J. McKendrick, and D. R. Wilson,Chem. Soc. Rev.,7, 65 (1978).Google Scholar
  12. 12.
    C. K. Johnson, Fr. Patent 1530511 (1968);Chem. Abs.,71, 13,717 (1969).Google Scholar
  13. 13.
    F. B. Wilson, Ph. D. Thesis, Glasgow University (1971).Google Scholar
  14. 14.
    F. Imashiro, M. Yoshimura, and T. Fujiwara,Acta Crystallogr.,C54, 1357 (1998) (structure of unsolvated form of1 from dodecane).Google Scholar
  15. 15.
    B. J. Brienne and J. Jacques,Tetrahedron Lett., 2349 (1975).Google Scholar
  16. 16.
    For the close packing principle see: A. I. Kitaigorodsky,Molecular Crystals and Molecules, Academic Press, London (1973).Google Scholar
  17. 17.
    R. H. Blessing,Acta Crystallogr.,51A, 33 (1995).Google Scholar
  18. 18.
    G. M. Sheldrick,SADABS, Bruker AXS, Madison (1997).Google Scholar
  19. 19.
    SMART V5.05J and SAINT V5.00, Area Detector Control and Integration Software, Bruker AXS, Madison (1998).Google Scholar
  20. 20.
    G. M. Sheldrick,SHELXTL-97 V5.10, Bruker AXS, Madison (1997).Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • T. W. Beresford
    • 1
  • C. S. Frampton
    • 1
  • J. H. Gall
    • 1
  • D. D. MacNicol
    • 1
  1. 1.Roche Discovery WelwynUniversity of GlasgowWelwyn Garden CityGreat Britain

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