Russian Chemical Bulletin

, Volume 44, Issue 6, pp 1005–1010 | Cite as

Spectroscopic and quantum chemical investigation of enol-enol tautomerism of 2-acetyltetronic acid

  • V. G. Avakyan
  • V. V. Gromak
  • A. E. Yatsenko
  • A. N. Shchegolikhin
  • N. A. Kubasova
Physical Chemistry

Abstract

Vibratonal spectra of 2-acetyltetronic acid (ATA) (3-acetyloxolane-2,4-dione) were investigated in different aggregate states.Ab initio quantum chemical calculations (3-21G basis set) of 2-formyltetronic acid as analogue of ATA and semi empirical calculation of ATA were carried out. The tautomeric forms of ATA can be arranged in the following series with respect to thermodynamic stability (in decresing order):1a,1b,2a,2b.

Key words

tautomerim of β,β′-triketones 2-acetyltetronic acid vibrational spectra quantum-chemical calculation intramolecular hydrogen bond 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. A. Akhrem and F. A. Lakhvich,Tesisy dokl. na IV Vsesoyusnoj Konf. po Khimii β-dikarbonilnykh soedinenii [IV All-Union Conf. on Chemistry of β-Dicarbonyl Compounds]. Abstracts of Papers. Zinatne, Riga, 1976, 11 (in Russian).Google Scholar
  2. 2.
    A. A. Avetisyan and M. T. Dangyan,Usp. Khim., 1977,64, 1250 [Russ. Chem. Rev., 1977,64 (Engl. Transl.)].Google Scholar
  3. 3.
    T. Yamaguchi, K. Saito, T. Tsujimoto, and H. Yuki,J. Heteroyclic Chem., 1976,13, 533.Google Scholar
  4. 4.
    V. Z. Kurbako, V. V. Gromak, V. G. Avakyan, and S. V. Rykov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1358 [Bull. Acad. Sci. SSSR, Div. Chem. Sci., 1991,40, 1199 (Engl. Transl.)].Google Scholar
  5. 5.
    S. Forsen, F. Mereniy, and M. Nilsson,Acta Chem. Scand., 1964,18, 1208.Google Scholar
  6. 6.
    V. G. Avakyan, V. V. Gromak, and V. Z. Kurbako,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2337 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 2188 (Engl. Transl.)].Google Scholar
  7. 7.
    S. Forsen, F. Merenyi, and M. Nilsson,Acta Chem. Scand., 1967,21, 620.Google Scholar
  8. 8.
    Ye. V. Borisov, T. S. Khlebnikova, D. V. Rubinov, and F. A. Lahvich,Zh. Org. Khim., 1992,28, 1306 [J. Org. Chem. USSR, 1992,28 (Engl. Transl.)].Google Scholar
  9. 9.
    V. G. Avakyan, V. V. Gromak, and A. E. Yatsenko,Izv. Akad. Nauk, Ser. Khim., 1994, 57 [Russ. Chem. Bull., 1994,43, 50 (Engl. Transl.)].Google Scholar
  10. 10.
    D. Ellis, P. J. Hendra, C. M. Hodges, T. Jawhari, C. Jones, P. Le Barazer, C. Passingham, I. A. M. Royaud, A. Sanchez-Blasquez, and G. Warnes,Analyst, 1989,114, 1061.Google Scholar
  11. 11.
    V. G. Avakyan and O. V. Fateyev,J. Mol. Struct. (THEOCHEM), 1992,262, 39.Google Scholar
  12. 12.
    M. J. S. Dewar, E. G. Zoebisch, and J. J. R. Stewart,J. Am. Chem. Soc., 1985,107, 3902Google Scholar
  13. 13.
    V. G. Avakyan and O. V. Fateyev,Izv. Akad. Nauk SSSR, Ser. Khim., 1993, 100 [Russ. Chem. Bull., 1993,42, 90 (Engl. Transl.)].Google Scholar
  14. 14.
    L. Bellamy,New Data on IR Spectra of Complex Molecules, Halsted Press, New York, 1968, 147.Google Scholar
  15. 15.
    Chemical Application of Spectroscopy, Ed. W. West, Interscience Publishers, Inc., New York, 1956.Google Scholar
  16. 16.
    L. Bellamy,Infrared Spectra of Complex Molecules, Wiley, New York, 1954, p. 57.Google Scholar
  17. 17.
    L. A. Duncanson,J. Chem. Soc., 1953, 1207.Google Scholar
  18. 18.
    S. F. Tayyari, T. Zeegers-Huyskins, and J. L. Wood,Spectrochim. Acta, 1979,35A, 1265.Google Scholar
  19. 19.
    K. A. K. Ebraheem, S. T. Hamdi, and M. N. Khalaf,Can. J. Spectrosc., 1981,26, 225.Google Scholar
  20. 20.
    H. C. Brown, J. H. Brewster, and H. Shechter,J. Am. Chem. Soc., 1954,76, 467.Google Scholar

Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • V. G. Avakyan
    • 1
  • V. V. Gromak
    • 2
  • A. E. Yatsenko
    • 1
  • A. N. Shchegolikhin
    • 3
  • N. A. Kubasova
    • 1
  1. 1.Institute of Petrochemical SynthesisRussian Academy of SciencesMoscowRussian Federation
  2. 2.Institute of Bioorganic ChemistryAcademy of Sciences of Belarus'MinksBelarus'
  3. 3.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations