Monatshefte für Chemie / Chemical Monthly

, Volume 127, Issue 5, pp 495–504 | Cite as

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

  • S. Stoyanov
  • T. Stoyanova
  • L. Antonov
  • P. Karagiannidis
  • P. Akrivos
Anorganische Und Physikalische Chemie

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.

Keywords

Pyridine and pyrimidine derivatives Symmetrical disulfides Thiol-disulfide interchange Thione-thiol tautomerism UV/Vis spectroscopy 

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

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).

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Copyright information

© Springer-Verlag 1996

Authors and Affiliations

  • S. Stoyanov
    • 1
  • T. Stoyanova
    • 1
  • L. Antonov
    • 1
  • P. Karagiannidis
    • 2
  • P. Akrivos
    • 2
  1. 1.Department of ChemistryUniversity of SofiaSofiaBulgaria
  2. 2.Department of General and Inorganic ChemistryAristotelian University of ThessalonikiThessalonikiGreece

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