Skip to main content
SpringerLink
Log in

Complexation of Ethanol by a Helical Tubuland Diol Host

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The cage compound 4,7-dimethylpentacyclo[6.3.0.02,6.03,10.05,9]undecane-anti-4,anti-7-diol 3 and its 4,7-bis(d 3-methyl) derivative 4 form 1:1 cocrystalline complexes with ethanol instead of the expected helical tubulate inclusion compounds. The X-ray crystal structure of (4)·(ethanol) [(C13H12D6O2)·(C2H6O), Cmca, a 19.049(2), b 14.932(2), c 10.117(1) Å, Z 8, R 0.061] shows that the key supramolecular synthon is a hydrogen-bonded (O — H)6 cycle of hydroxy groups constructed from two ethanols (in ring positions 1 and 4) and four diols. This uncommon centrosymmetric motif permits efficient lattice packing of ethanol and both diol enantiomers into layers without requiring the self-resolution that would be mandatory in forming the helical tubulate structure.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Bishop, R. In Comprehensive Supramolecular Chemistry, vol. 6; MacNicol, D. D.; Toda, F.; Bishop, R., eds.; Pergamon Press: Oxford, 1996; pp. 85-115.

    Google Scholar 

  2. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.

    Google Scholar 

  3. MacNicol, D. D.; McKendrick, J. J.; Wilson, D. R. Chem. Soc. Rev. 1978, 7, 65-87.

    Google Scholar 

  4. Inclusion Compounds; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D., eds.; Academic Press: London, 1984; vols. 1–3; and Oxford University Press: Oxford, 1991; vols. 4–5.

    Google Scholar 

  5. Bishop, R.; Dance, I. G.; Hawkins, S. C.; Scudder, M. L. J. Inclusion Phenom. 1987, 5, 229-232.

    Google Scholar 

  6. Bishop, R.; Craig, D. C.; Scudder, M. L.; Marchand, A. P.; Liu, Z. J. Chem. Soc., Perkin Trans. 1995, 2, 1295-1300.

    Google Scholar 

  7. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids, Materials Science Monographs No. 54; Elsevier: Amsterdam, 1989.

    Google Scholar 

  8. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981, ch. 2.

    Google Scholar 

  9. Ung, A. T.; Gizachew, D.; Bishop, R.; Scudder, M. L.; Dance, I. G.; Craig, D. C. J. Am. Chem. Soc. 1995, 117, 8745-8756.

    Google Scholar 

  10. Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. Chem. Mater. 1994, 6, 1269-1281.

    Google Scholar 

  11. Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L., Marchand, A. P.; Wang, Y. J. Chem. Soc., Perkin Trans. 1993, 2, 937-943.

    Google Scholar 

  12. Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comp. Sci. 1991, 31, 187-204.

    Google Scholar 

  13. Mak, T. C. W.; Bracke, B. R. F. In Comprehensive Supramolecular Chemistry, vol. 6; MacNicol, D. D.; Toda, F.; Bishop, R., eds.; Pergamon Press: Oxford, 1996; pp. 23-60.

    Google Scholar 

  14. MacNicol, D. D. In Inclusion Compounds, vol. 2; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D., eds.; Academic Press: London, 1984; pp. 124-168.

    Google Scholar 

  15. Finocchiaro, P.; Failla, S. In Comprehensive Supramolecular Chemistry, vol. 6; MacNicol, D. D.; Toda, F.; Bishop, R., eds.; Pergamon Press: Oxford, 1996; pp. 593-642.

    Google Scholar 

  16. Peters, C. Y.; Jensen, W. P.; Worman, J. J.; Jacobson, R. A.; Nelson, D. A. J. Heterocycl. Chem. 1977, 14, 769-775.

    Google Scholar 

  17. Ferguson, G.; McCrindle, R.; McAlees, A. J. Can. J. Chem. 1989, 67, 779-785.

    Google Scholar 

  18. Hawkins, S. C.; Scudder, M. L.; Craig, D. C.; Rae, A. D.; Abdul Raof, R. B.; Bishop, R.; Dance, I. G. J. Chem. Soc., Perkin Trans. 2, 1990, 855-870.

    Google Scholar 

  19. Weber, E.; Dörpinghaus, N.; Wimmer, C.; Stein, Z.; Krupitsky, H.; Goldberg, I. J. Org. Chem. 1992, 57, 6825-6833.

    Google Scholar 

  20. Smith, E. C.; Barborak, J. C. J. Org. Chem. 1976, 41, 1433-1437.

    Google Scholar 

  21. Herath Banda, R. M.; Dance, I. G.; Bailey, T. D.; Craig, D. C.; Scudder, M. L. Inorg Chem. 1989, 28, 1862-1871.

    Google Scholar 

  22. De Meulenaer, J.; Tompa, H. Acta Crystallogr. 1965, 19, 1014-1018.

    Google Scholar 

  23. Main, P.; Fiske, S. J.; Hull, L.; Lessinger, L.; Germain, G.; Declercq, J.-P.; Woolfson, M. M. MULTAN80; Universities of York, England, and Louvain, Belgium, 1980.

    Google Scholar 

  24. Rae, A. D. RAELS. A Comprehensive Constrained Least Squares Refinement Program; University of New South Wales, 1989.

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, The University of New South Wales, Sydney, 2052, Australia

    Paul D. Ahn, Roger Bishop, Donald C. Craig & Marcia L. Scudder

Authors
  1. Paul D. Ahn
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Roger Bishop
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Donald C. Craig
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marcia L. Scudder
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ahn, P.D., Bishop, R., Craig, D.C. et al. Complexation of Ethanol by a Helical Tubuland Diol Host. Structural Chemistry 10, 169–176 (1999). https://doi.org/10.1023/A:1021880328629

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1021880328629

Search

Navigation