Skip to main content
SpringerLink
Log in

Thione-disulfide interchange of some heterocyclic tautomeric thiones and their symmetrical disulfides

Thion-Disulfid-Umwandlung einiger heterocyclischer tautomerer Thione und ihrer symmetrischen Disulfide

  • Anorganische Und Physikalische Chemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The UV/Vis spectroscopic properties of some symmetrical disulfides derived from potentially tautomeric thiones are investigated. Reversed thione-disulfide transformation is observed, and the influence of several factors including the nature of solvent, concentration, and UV irradiation, is studied. Possible implication of the tautomeric thiol form and the importance of this thione-disulfide redox system in biological aspects is suggested. A general scheme including monomer-dimer equilibrium, thione-thiol tautomeric equilibrium, and reversible thiol-disulfide redox behaviour is proposed in order to explain the factors affecting the overall thione-disulfide transformation.

Zusammenfassung

Die UV/Vis-spektroskopischen Eigenschaften einiger symmetrischer Disulfide, die als Derivate von potentiell tautomeren Thionen auftreten, wurden untersucht. Es wurde eine reversible Thion-Disulfid-Transformation beobachtet. Der Einfluß einiger Faktoren wie Natur des Lösungsmittels, Konzentration und UV-Bestrahlung wurden erforscht. Die Bedeutung des untersuchten Redoxsystems in biologischer Hinsicht wird diskutiert. Um die Auswirkung der einzelnen Faktoren auf die Umsetzung zu erklären, wird ein allgemeines Schema vorgeschlagen (Monomer-Dimer-Gleichgewicht, Thion-Thiol-Gleichgewicht, reversibles Thiol-Disulfid-Redoxsystem).

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. Katritzky AR, Lagowski JM (1963) Adv Heterocycl Chem1: 312

    Google Scholar 

  2. Marshall R, Walker J (1951) J Chem Soc 1004

  3. Bearland PV, McOmie JFW (1952) J Chem Soc 3716

  4. Albert A, Barlin GB (1959) J Chem Soc 2384

  5. Jones RA, Katritzky AR (1958) J Chem Soc 3610

  6. Korobkov VS, Voropaeva V, Feldman IH (1961) Zh Obshch Khim31: 3136

    Google Scholar 

  7. Albert A, Barlin GB (1959) J Chem Soc 3129

  8. Beak P, Fry IS Jr, Lee J, Steela F (1976) J Am Chem Soc98: 171

    Google Scholar 

  9. Elguero J, Marzin C, Katritzky AR, Linda P (1976) The Tautomerism of Heterocycles. In: Katritzky AR, Boulton AJ (eds) Adv Heterocycl Chem Suppl 1. Academic Press, New York, chapter 2

    Google Scholar 

  10. Beak P, Covington JB, Smith SG (1976) J Am Chem Soc98: 8284

    Google Scholar 

  11. Beak P (1977) Acc Chem Res10: 186

    Google Scholar 

  12. Beak P, Covington JB, Smith SG, White JM, Zeiger JM (1980) J Org Chem45: 1354

    Google Scholar 

  13. Renfold BR (1953) Acta Crystallogr6: 707

    Google Scholar 

  14. Ohms UH, Guth H, Kutoglu A, Scheringer C (1982) Acta Crystallogr, Sect B: Struct Crystallogr Cryst ChemB38: 831

    Google Scholar 

  15. Ohno A, Oae S (1977) In: Oae S (ed) Organic Chemistry of Sulfur. Plenum Press, New York London, p 155

    Google Scholar 

  16. Reid EE (1960) Organic Chemistry of Bivalent Sulfur, vol 3. Chemical Publ Co, New York, pp 362–462

    Google Scholar 

  17. Stoyanov S, Petkov I, Antonov L, Stoyanova T, Karagiannidis P, Aslanidis P (1990) Can J Chem68: 1482

    Google Scholar 

  18. Kitson TM (1988) J Chem Educ65: 829

    Google Scholar 

  19. Brocklenurst K (1982) Methods Enzylmol87C: 427

    Google Scholar 

  20. King H, Ware LL (1939) J Chem Soc 873

  21. Mackwald W, Klemm W, Trabert H (1900) Chem Ber33: 1559

    Google Scholar 

  22. Renault J (1955) Ann Chem10: 135

    Google Scholar 

  23. Elguero J, Marzin C, Katritzky AR, Linda P (1976) The Tautomerism of Heterocycles. In: Katritzky AR, Boulton AJ (eds) Adv Heterocycl Chem Suppl 1. Academic Press, New York, p 7

    Google Scholar 

  24. Perkampus HH (1992) UV/VIS Spectroscopy and Its Applications. Springer, Berlin, chapter 7.1.1

    Google Scholar 

  25. Reichardt C (1990) Solvents and Solvent Effects in Organic Chemistry. VCH Weinheim, p 63

    Google Scholar 

  26. Getoff N (1993) Proc Indian Acad Sci (Chem Sci), vol 105, pp 373–391

    Google Scholar 

  27. Becker GO (1976) Einführung in die Photochemie. VEB, Berlin, p 167

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Sofia, BG-1126, Sofia, Bulgaria

    S. Stoyanov, T. Stoyanova & L. Antonov

  2. Department of General and Inorganic Chemistry, Aristotelian University of Thessaloniki, GR-54006, Thessaloniki, Greece

    P. Karagiannidis & P. Akrivos

Authors
  1. S. Stoyanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. Stoyanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. Antonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. Karagiannidis
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. Akrivos
    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

Stoyanov, S., Stoyanova, T., Antonov, L. et al. Thione-disulfide interchange of some heterocyclic tautomeric thiones and their symmetrical disulfides. Monatsh Chem 127, 495–504 (1996). https://doi.org/10.1007/BF00807074

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807074

Keywords

Search

Navigation