Skip to main content
SpringerLink
Log in

Electronic Structure of π Systems: XX. Electronic Structure and Keto-Enol Tautomerism of Dihydrofuro[2,3-h]- coumarin-9-ones by Photoelectron Spectroscopy

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Photoelectron spectroscopy and semiempirical quantum-chemical calculations were used to study the electronic structure and keto-enol tautomerism of 4-methyldihydrofuro[2,3-h]coumarin-9-one and its 8-substituted derivatives. Analysis of the electronic structure of 8,8-dibromo-4-methyldihydrofuro[2,3-h]-coumarin-9-one (fixed keto form) and 9-acetoxy-4-methylangelicin (fixed enol form) allowed to reveal ionization ranges for the corres ponding tautomeric forms. All dihydrofuro[2,3-h]coumarin-9-ones studied were found to exist in the gas phase exclusively in the keto form.

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. Safronova, O.B., Kravchenko, D.V., Senchenya, I.N., and Traven', V.F., Zh. Obshch. Khim., 2001, vol. 71, no. 4, pp. 588-595.

    Google Scholar 

  2. Ghosh, P.K., Introduction to Photoelectron Spectroscopy, New York: Willey, 1983.

    Google Scholar 

  3. Traven, V.F., Frontier Orbitals and Properties of Organic Molecules, Chichester: Horwood, 1992.

    Google Scholar 

  4. Schweing, A., Vermeer, H., and Weidner, U., Chem. Phys. Lett., 1976, vol. 26, pp. 229-234.

    Google Scholar 

  5. Guimon, G., Tetrahedron Lett., 1979, vol. 28, p. 2585.

    Google Scholar 

  6. Turchaninov, V.K., Danovich, D.K., Ermikov, A.F., and Andriyanenkov, M.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1992, no. 4, pp. 872-878.

    Google Scholar 

  7. Traven', V.F., Manaev, A.V., Safronova, O.B., Chibisova, T.A., Lysenko, K.A., and Antipin, M.Yu., Zh. Obshch. Khim., 2000, vol. 70, no. 5, pp. 853-864.

    Google Scholar 

  8. Traven, V.F., Kravtchenko, D.V., Chibisova, T.A., Shorshnev, S. V., Eliason, R., and Wakefield, D.H., Heterocycl. Commun., 1996, vol. 2, no. 4, pp. 345-354.

    Google Scholar 

  9. Koopmans, T., Physica, 1934, vol. 1, pp. 104-113.

    Google Scholar 

  10. Traven', V.F., Safronov, A.I., and Chibisova, T.A., Zh. Obshch. Khim., 1991, vol. 61, no. 3, pp. 697-705.

    Google Scholar 

  11. Vovna, V.I. and Vilesov, F.I., Usp. Fotoniki, 1975, no. 5, pp. 3-149.

    Google Scholar 

  12. Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., and Stewart, J.J.P., J. Am. Chem. Soc., 1985, vol. 107, no. 13, pp. 3902-3909.

    Google Scholar 

  13. Kravtchenko, D.V., Chibisova, T.A., and Traven, V.F., Heterocycl. Commun., 1997, vol. 3, no. 4, pp. 331-338.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Mendeleev Russian University of Chemical Technology, Moscow, Russia

    V. F. Traven', A. V. Manaev, D. V. Kravchenko & T. A. Chibisova

Authors
  1. V. F. Traven'
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Manaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. V. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. A. Chibisova
    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

Traven', V.F., Manaev, A.V., Kravchenko, D.V. et al. Electronic Structure of π Systems: XX. Electronic Structure and Keto-Enol Tautomerism of Dihydrofuro[2,3-h]- coumarin-9-ones by Photoelectron Spectroscopy. Russian Journal of General Chemistry 71, 945–949 (2001). https://doi.org/10.1023/A:1012347905664

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012347905664

Keywords

Search

Navigation