Russian Chemical Bulletin

, Volume 48, Issue 4, pp 686–689 | Cite as

Reductive cleavage of dichalcogenide bonds

2. Electrochemistry of bridged bispyridinium systems, electrochemical catalysts of reduction of organic dichalcogenides
  • G. V. Loukova
  • E. P. Olekhnovich
  • M. E. Kletzky
  • A. A. Bumber
  • A. D. Garnovskii
Physical Chemistry
  • 34 Downloads

Abstract

Electrochemical reduction of 1,2-di(2,4,6-triphenylpyridinium-l)ethane, 1,4-di(2,4,6-triphenylpyridinium-1)butane, 1,6-di(2,4,6-triphenylpyridinium-l)hexane, 1,4-di(N-methyl-4,6-diphenylpyridinium-2)benzene, and 2,7-di(N-methyl-4,6-diphenylpyridinium-2)fluorene in solutions of DMF and MeCN in the potential range from−0.8 to −1.7 V (SCE) was studied by CV. The successive formation of stable radical cations, biradicals, and dianions was investigated by semiempirical MO calculations at the PM3 level.

Key words

bispyridinium, redox catalysis dichalcogenide bond cleavage cyclic voltammetry quantum-chemical analysis, semiempirical methods 

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References

  1. 1.
    G. V. Loukova, A. A. Bumber, A. S. Burlov, E. P. Olekhnovich, and A. D. Garnovskii,Zh. Obshch. Khim., 1998,68, 637 [Russ. J. Gen. Chem., 1998,68 (Engl. Transl.)].Google Scholar
  2. 2.
    D. J. McClemens, A. K. Garrison, and A. L. Underwood,J. Org. Chem., 1969,34, 1867.CrossRefGoogle Scholar
  3. 3.
    P. N. Crawford, W. O. Poye, and M. D. Ryan,J. Pharm. Sci., 1987,76, 481.Google Scholar
  4. 4.
    P. S. Braterman and J.-I. Sog,J. Org. Chem., 1991,56, 4678.CrossRefGoogle Scholar
  5. 5.
    A. Anne, P. Hapiot, J. Moiroux, and J.-M. Saveant,J. Electroanal. Chem., 1992,331, 959.CrossRefGoogle Scholar
  6. 6.
    L. Stryer,Biochemistry, W. H. Freeman and Co., San Francisco, 1981,2, 267.Google Scholar
  7. 7.
    R. S. Nicholson and I. Shain,Anal. Chem., 1964,36, 706.CrossRefGoogle Scholar
  8. 8.
    A. J. Fry, T. A. Powers, K. Muller, and W. Irmen,Tetrahedron Lett., 1985,26, 4879.CrossRefGoogle Scholar
  9. 9.
    K. R. Stickley, T. D. Selby, and S. C. Blackstock,J. Org. Chem., 1997,62, 448.CrossRefGoogle Scholar
  10. 10.
    F. Ammar and J.-M. Saveant,J. Electroanal. Chem., 1973,47, 215.Google Scholar
  11. 11.
    J. B. Flanagan, S. Margel, A. J. Bard, and F. C. Anson,J. Am. Chem. Soc., 1978,100, 4248.CrossRefGoogle Scholar
  12. 12.
    A. J. Bard and L. R. Faulkner,Electrochemical Methods: Fundamentals and Applications, J. Wiley and Sons, New York, 1980, Chs. 6, 11.Google Scholar
  13. 13.
    J. J. P. Stewart,J. Comput. Chemistry, 1989,10, 221.CrossRefGoogle Scholar
  14. 14.
    J. J. P. Stewart,MOPAC-7.0: A Semiempirical Molecular Orbital Program. Program N 455, Quantum Chemistry Program Exchange (QCPE), Indiana University, Bloomington, IN 47405, USA.Google Scholar
  15. 15.
    V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev,Kvantovaya khimiya organicheskikh soedinenii. Mekhanizmy reaktsii [Quantum Chemistry of Organic Compounds. Mechanisms of Reactions], Khimiya, Moscow, 1986, Ch. 2 (in Russian).Google Scholar
  16. 16.
    B. Ya. Simkin and I. Sheikhet,Quantum Chemical and Statistical Theory of Solutions, Ellis Horwood Ltd., London, 1995, 266.Google Scholar
  17. 17.
    A. A. Arutyunyants, A. A. Bumber, L. B. Dzaraeva, A. V. Shpakov, S. E. Emanuilidi, and E. S. Klimov,Vysokomol. Soedin., A, 1989,31, 258 [Polym. Sci. USSR, A, 1989,31 (Engl. Transl.)].Google Scholar
  18. 18.
    A. F. Pozharskii, V. A. Anisimova, and E. B. Tsupak,Prakticheskie raboty po khimii geterotsiklov [Pructical Works on Chemistry of Heterocycles], Izd-vo Rostovskogo Gos. Univ., Rostov-on-Don, 1988, 53 pp. (in Russian).Google Scholar
  19. 19.
    G. N. Dorofeenko, E. I. Sadekova, and E. V. Kuznetsov,Preparativnaya khimiya pirilievykh solei [Preparative Chemistry of Pyrilium Salts], Izd-vo Rostovskogo Gos. Univ., Rostov-on-Don, 1972, 120 pp. (in Russian).Google Scholar
  20. 20.
    A. J. Bard, E. Garcia, S. Kukharenko, and V. V. Strelets,Inorg. Chem., 1993,32, 3528.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • G. V. Loukova
    • 1
  • E. P. Olekhnovich
    • 2
  • M. E. Kletzky
    • 3
  • A. A. Bumber
    • 3
  • A. D. Garnovskii
    • 2
  1. 1.Institute of Problems of Chemical PhysicsRussian Academy of SciencesChernogolovka, Moscow RegionRussian Federation
  2. 2.Research Institute of Physical and Organic ChemistryRostov State UniversityRostov-on-DonRussian Federation
  3. 3.Rostov State UniversityRostov-on-DonRussian Federation

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