Chemistry of Natural Compounds

, Volume 11, Issue 5, pp 613–616 | Cite as

Ultraviolet absorption of flavonoids. V. The structure of 3- and 5-hydroxyflavones

  • N. A. Tyukavkina
  • N. N. Pogodaeva
  • E. I. Brodskaya
  • Yu. M. Sapozhnikov


1. The peculiarities of the properties of 3-hydroxyflavone are due to the fact that the introduction of the proton-donating hydroxy group directly into the heterocycle leads to an increase in the aromaticity of the pyrone fragment through the stabilization of a pyrylium structure.

2. The causes of the decreased acidity and basicity of 5-hydroxyflavone are the formation of an intramolecular hydrogen bond of the chelate type and a disturbance of the coplanarity of the molecule. The combination of these factors explains the anomalously high position of the band of the stretching vibrations of the carbonyl group of this compound.


Carbonyl Group Flavone Hydroxy Group Intramolecular Hydrogen Bond Methyl Ether 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    N. A. Tyukavkina and N. N. Pogodaeva, Khim. Prirodn. Soedin., 11 (1971).Google Scholar
  2. 2.
    N. A. Tyukavkina and N. N. Pogodaeva, Khim. Prirodn. Soedin., 173 (1972).Google Scholar
  3. 3.
    N. N. Pogodaeva and N. A. Tyukavkina, Khim. Prirodn. Soedin., 25 (1973).Google Scholar
  4. 4.
    J. M. Looker and W. W. Hanneman, J. Org. Chem.,27, 381 (1962).CrossRefGoogle Scholar
  5. 5.
    L. H. Briggs and L. D. D. Colebrook, Spectrochim. Acta,18, 939 (1962).CrossRefGoogle Scholar
  6. 6.
    E. M. Nevskaya and V. A. Nazarenko, Zh. Analit. Khim.,27, 1699 (1972).Google Scholar
  7. 7.
    E. M. Arnett and C. Y. Wu, J. Amer. Chem. Soc.,84, 1684 (1962).CrossRefGoogle Scholar
  8. 8.
    E. R. David, G. Y. Litke, and R. Bognar, Acta. Univ. Debrecen, Ser. Phys. Chem.,17, 215 (1971).Google Scholar
  9. 9.
    R. D. H. Murray and P. H. McCabel, Tetrahedron,25, 5819 (1969).CrossRefGoogle Scholar
  10. 10.
    R. D. H. Murray, P. H. McCabel, and T. C. Hogg, Tetrahedron,25, 5839 (1969).CrossRefGoogle Scholar
  11. 11.
    L. Bellamy, Advances in Infrared Group Frequencies, Methuen, London (1968).Google Scholar
  12. 12.
    M. Bellamy, Infrared Spectra of Complex Molecules, 2nd ed., Methuen, London/J. Wiley, New York (1958).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • N. A. Tyukavkina
  • N. N. Pogodaeva
  • E. I. Brodskaya
  • Yu. M. Sapozhnikov

There are no affiliations available

Personalised recommendations