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Electroreduction of Organic Compounds with Two Reactive Centers. I. 1,2,4-Triazines

  • Petr Zuman
  • František Riedl
  • František Liška
  • Jiří Ludvík
Conference paper

Abstract

In most organic molecules a conjugation of two adjacent double bonds facilitates the electroreduction of the more easily reducible group. An exception of this rule has been observed for some 1,2,4-triazines In two model compounds metamitron(I) (4-amino-3-methyl-6-Phenyl-1,2,4-triazin-5(4H)-one) and metribuzin(II) (4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one), which cannot undergo tautomeric changes, two azomethine bonds are present. Their electrochemical reduction on mercury electrodes occurs in two two-electron steps. The 1,6-bond C=N is reduced in protic solvents in the protonated form at potentials by about 0.5 V more positive than the protonated C=N bond in position 2, 3. Potentials of both reduction steps are shifted with increasing pH to more negative values, limiting currents of both steps decrease with increasing pH in a potential range where the protonotion becomes insufficiently fast. Limiting currents of both steps are affected by covalent hydration.

Keywords

Czech Republic Nitrogen Atom Organic Molecule Potential Range Sodium Borohydride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Petr Zuman
    • 1
  • František Riedl
    • 2
  • František Liška
    • 3
  • Jiří Ludvík
    • 2
  1. 1.Department of ChemistryClarkson UniversityPotsdamUSA
  2. 2.J. Heyrovský Inst. of Physical ChemistryPrague 8Czech Republic
  3. 3.Department of Organic ChemistryInst. of Chemical Tech.Prague 6Czech Republic

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