Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Article
  • Published:

Self-association of Phenolics and of Bile Acid Derivatives

Abstract

Spectral Investigations of certain polyfunctional phenolic compounds and of derivatives of the bile acids, using infra-red, ultra-violet and nuclear magnetic resonance techniques, reveal abnormally persistent intermolecular self-association through multiple hydrogen bonding. The extent of the effect, as measured by osmometry, depends on the stereochemistry of the molecules involved, especially the position and number of attached hydroxyl groups.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Nakanishi, K., Infrared Absorption Spectroscopy: Practical (Holden-Day, Inc., San Francisco, 1964).

    Google Scholar 

  2. Tichy, M., in Adv. Org. Chem., 5, 115 (Interscience, New York, 1965). West, R., Korst, I. J., and Johnson, W. S., J. Org. Chem., 25, 1976 (1960).

    CAS  Google Scholar 

  3. Henbest, H. B., Meakins, G. D., and Wrigley, T. I., J. Chem. Soc., 2633 (1958).

  4. Baker, A. J., Eglinton, G., Gonzalez, A. G., Hamilton, R. J., and Raphael, R. A., J. Chem. Soc., 4705 (1962).

  5. Pitha, J., Joska, J., and Fajkos, J., Coll. Czech. Chem. Commun., 28, 2611 (1963).

    Article  CAS  Google Scholar 

  6. Cairns, T., Eglinton, G., Scott, A. I., and Young, D. W., J. Chem. Soc., B, 654 (1966).

  7. Anet, F. A. L., and Muchowski, J. M., Proc. Chem. Soc., 219 (1962).

  8. Brown, I., Eglinton, G., and Martin-Smith, M., J. Chem. Soc., 2551 (1963).

  9. Page, J. E., and Robertson, F. A., J. Chem. Soc., 133 (1943).

  10. Datta, N. P., J. Ind. Chem. Soc., 16, 573 (1939).

    CAS  Google Scholar 

  11. Bellamy, L. J., Lake, R. F., and Pace, R. J., Spectrochim. Acta, 19, 443 (1963).

    Article  ADS  CAS  Google Scholar 

  12. Cairns, T., and Eglinton, G., Nature, 196, 535 (1963); J. Chem. Soc., 5906 (1965).

    Article  ADS  Google Scholar 

  13. Norman, A., Acta Chem. Scand., 14, 1295 (1960).

    Article  CAS  Google Scholar 

  14. Nyström, E., and Sjoväll, J., Anal. Biochem., 12, 235 (1965). Also chapters by Sjoväll in Methods of Biochemical Analysis (edit. by Glick, D.) (Wiley, New York, 1964) and New Biochemical Separations (edit. by Morris, L. G., and James, A. T.) (Van Nostrand, 1964).

    Google Scholar 

  15. Kempter, H., and Mecke, R., Z. Physik. Chem., B, 46, 229 (1940).

    Google Scholar 

  16. Hagan, M., Clathrate Inclusion Compounds, 15 (Rheinhold Publishing Corp., New York, 1962). Bhatnagar, V. M., Chemical Age of India, 15, 827 (1964).

    Google Scholar 

  17. Wieland, H., and Sorge, H., Z. Physiol. Chem., 97, 1 (1916).

    Article  CAS  Google Scholar 

  18. Go, Y., and Kratky, O., Z. Physik. Chem., B, 26, 439 (1934).

    Google Scholar 

  19. Kratky, O., and Giacomello, G., Monatsh, 69, 427 (1936).

    Article  CAS  Google Scholar 

  20. Angyal, S. J., and Young, R. J., J. Amer. Chem. Soc., 81, 5251 (1959).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

BENNET, W., EGLINTON, G. & KOVAC, S. Self-association of Phenolics and of Bile Acid Derivatives. Nature 214, 776–780 (1967). https://doi.org/10.1038/214776a0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/214776a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing