Skip to main content
SpringerLink
Log in

Tautomerism of anthraquinones: IV. 1-Hydroxy-9,10-anthraquinone and its substituted derivatives

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

Abstract

1-Hydroxyanthraquinone and its substituted derivatives exist as equilibrium mixtures of four tautomers and rotational isomers. Their anions have 9,10-and 1,10-quinoid structures. Each tautomer or conformer is characterized by a single π1,π* band in the electronic absorption spectrum.

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. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Org. Chem., 2006, vol. 42, p. 1464.

    CAS  Google Scholar 

  2. Fain, V.Ya., 9,10-Antrakhinony i ikh primenenie (9,10-Anthraquinines and Their Aplication), Moscow: Tsentr Fotokhimii Ross. Akad. Nauk, 1999.

    Google Scholar 

  3. Fain, V.Ya., Korrelyatsionnyi analiz elektronnykh spektrov pogloshcheniya (Correlation Analysis of Electronic Absorption Spectra), Moscow: Sputnik+, 2002.

    Google Scholar 

  4. Fain, V.Ya., Elektronnye spektry pogloshcheniya i stroenie 9,10-antrakhinonov. I. 9,10-Antrakhinon i ego monozameshchennye (Electronic Absorption Spectra and Structure of 9,10-Anthraquinones.9, 10-Anthraquinone and Its Monosubstituted Derivatives), Moscow: Sputnik+, 2003.

    Google Scholar 

  5. Fain, V.Ya., Elektronnye spektry pogloshcheniya i stroenie 9,10-antrakhinonov. II. Dizameshchennye antrakhinony (Electronic Absorption Spectra and Structure of 9,10-Anthraquinones. Disubstituted 9,10-Anthraquinones), Moscow: Sputnik+, 2003.

    Google Scholar 

  6. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Org. Chem., 2005, vol. 41, p. 38.

    Article  CAS  Google Scholar 

  7. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Gen. Chem., 2003, vol. 73, p. 1925.

    Article  CAS  Google Scholar 

  8. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Gen. Chem., 2003, vol. 73, p. 1595.

    Article  CAS  Google Scholar 

  9. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Org. Chem., 2005, vol. 41, p. 707.

    Article  CAS  Google Scholar 

  10. Müller, A., Körmendy, K., Ruff, F., and Vajda, M., Acta Chim. Acad. Sci. Hung., 1969, vol. 59, p. 109.

    Google Scholar 

  11. Tokumitsu, T., Okamoto, J., and Hayashi, T., J. Soc. Synth. Org. Chem. Jpn., 1968, vol. 26, p. 890.

    CAS  Google Scholar 

  12. Morton, R.A., Biochemistry of Quinones, London: Academic, 1965, p. 51.

    Google Scholar 

  13. Thomson, R.H., Naturally Occurring Quinones, London: Academic, 1971, 2nd ed.

    Google Scholar 

  14. Atlas spektrov aromaticheskikh i geterotsiklicheskikh soedinenii, vyp. 16. Spektry pogloshcheniya proizvodnykh antrakhinona v infrakrasnoi, ul’trafioletovoi i vidimoi oblastyakh (Atlas of Spectra of Aromatic and Heterocyclic Compounds. Issue 16. Absorption Spectra of Anthraquinone Derivatives in the Infrared, Ultraviolet, and Visible Regions), Koptyug, V.A., Ed., Novosibirsk: Inst. Org. Khim. Sib. Otd. Akad. Nauk SSSR, 1978, p. 162.

    Google Scholar 

  15. Tessier, A.M., Delaveau, P., and Champion, B., Planta Med., 1981, vol. 41, p. 337.

    CAS  Google Scholar 

  16. Shcheglova, N.A., Shigorin, D.N., Nezhel’skaya, R.A., Galitsyna, L.V., and Dokunikhin, N.S., Zh. Fiz. Khim., 1974, vol. 48, p. 271.

    CAS  Google Scholar 

  17. Capitán, F., Román, M., and Martin Espigares, M., Quim. Industr., 1970, vol. 16, p. 7.

    Google Scholar 

  18. Metwally, S.A.M., J. Appl. Chem. Biotechnol., 1975, vol. 25, p. 161.

    Article  CAS  Google Scholar 

  19. Capitan, F., Salinaz, F., and Franquelo, L.M., Anal. Quim., 1976, vol. 72, p. 529.

    CAS  Google Scholar 

  20. Furuya, T., Kojima, H., and Katsuta, T., Phytochemistry, 1972, vol. 11, p. 1073.

    Article  CAS  Google Scholar 

  21. Arrebola, M.L., Ringbom, T., and Verpoorte, R., Phytochemistry., 1999, vol. 52, p. 1283.

    Article  CAS  Google Scholar 

  22. Broadbent, A.D. and Newton, R.P., Can. J. Chem., 1972, vol. 50, p. 381.

    Article  CAS  Google Scholar 

  23. Broadbent, A.D., Hewson, W.D., McDonald, H.A., and Melanson, R.J., Can. J. Chem., 1977, vol. 55, p. 2946.

    Article  CAS  Google Scholar 

  24. Fain, V.Ya., Zaitsev, B.E., and Ryabov, M.A., Russ. J. Gen. Chem., 2003, vol. 73, p. 621.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Russian University of Peoples’ Friendship, P.O. Box 453, Moscow, 127349, Russia

    V. Ya. Fain, B. E. Zaitsev & M. A. Ryabov

Authors
  1. V. Ya. Fain
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. E. Zaitsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Ryabov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © V.Ya. Fain, B.E. Zaitsev, M.A. Ryabov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 10, pp. 1484–1487.

For communication III, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fain, V.Y., Zaitsev, B.E. & Ryabov, M.A. Tautomerism of anthraquinones: IV. 1-Hydroxy-9,10-anthraquinone and its substituted derivatives. Russ J Org Chem 42, 1469–1472 (2006). https://doi.org/10.1134/S1070428006100113

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428006100113

Keywords

Search

Navigation