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Russian Chemical Bulletin

, Volume 60, Issue 11, pp 2131–2140 | Cite as

Chalcogen-nitrogen π-heterocyclic radical anion salts: the synthesis and properties

  • N. P. Gritsan
  • A. V. Zibarev
Reviews

Abstract

The review concerns methods of synthesis, as well as the molecular, electronic, and crystal structures and the magnetic properties of a novel class of paramagnetic compounds, namely, chalcogen-nitrogen π-heterocyclic radical anion salts derived from 1,2,5-chalcogenadiazole.

Key words

nitrogen radical anions antiferromagnetic compounds heterocycles paramagnetic compounds synthesis salts structure chalcogens 

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References

  1. 1.
    F. Troiani, M. Affronte, Chem. Soc. Rev., 2011 (doi: 10.1039/c0cs00158a).Google Scholar
  2. 2.
    Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds, Ed. R. G. Hicks, Wiley, New York, 2010.Google Scholar
  3. 3.
    D. Awschalom, Physics, 2009, 2, 50.CrossRefGoogle Scholar
  4. 4.
    F. Fert, Angew. Chem., Int. Ed., 2008, 48, 5956.CrossRefGoogle Scholar
  5. 5.
    G. Saito, Y. Yoshida, Bull. Chem. Soc. Jpn, 2007, 80, 1.CrossRefGoogle Scholar
  6. 6.
    J. S. Miller, Dalton Trans., 2006, 2747.Google Scholar
  7. 7.
    E. Coronado, D. Gatteschi, J. Mater. Chem., 2006, 16, 2513.CrossRefGoogle Scholar
  8. 8.
    R. P. Shibaeva, E. B. Yagubskii, Chem. Rev., 2004, 104, 5347 (and other materials in that issue).CrossRefGoogle Scholar
  9. 9.
    S. J. Blundell, F. L. Pratt, J. Phys.: Condensed Matter, 2004, 16, R771.CrossRefGoogle Scholar
  10. 10.
    E. B. Yagubskii, in Organic Conductors, Superconductor, and Magnets: From Synthesis to Molecular Electronics, Eds L. Ouahab, E. Yagubskii, Kluwer, Dordrecht, 2004, p. 45.CrossRefGoogle Scholar
  11. 11.
    V. A. Ivanov, T. G. Aminov, V. M. Novotortsev, V. T. Kalinnikov, Izv. Akad. Nauk. Ser. Khim., 2004, 2255 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2357].Google Scholar
  12. 12.
    J. S. Miller, Adv. Mater., 2002, 14, 1105.CrossRefGoogle Scholar
  13. 13.
    R. T. Boere, T. L. Roemmele, Coord. Chem. Rev., 2000, 210, 369.CrossRefGoogle Scholar
  14. 14.
    V. I. Ovcharenko, R. Z. Sagdeev, Usp. Khim., 1999, 68, 381 [Russ. Chem. Rev. (Engl. Transl.), 1999, 68].Google Scholar
  15. 15.
    T. Chivers, R. S. Laitinen, in Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium, Ed. F. Devillanova, RSC Press, Cambridge, 2007.Google Scholar
  16. 16.
    T. Chivers, A Guide to Chalcogen-Nitrogen Chemistry, World Scientific, Singapore, 2005.CrossRefGoogle Scholar
  17. 17.
    K. Lekin, S. M. Winter, L. E. Downie, X. Bao, J. S. Tse, S. Desgreniers, R. A. Secco, P. A. Dube, R. T. Oakley, J. Am. Chem. Soc., 2010, 132, 16212.CrossRefGoogle Scholar
  18. 18.
    C. S. Clarke, J. Jornet-Somoza, F. Mota, J. J. Novoa, M. Deumal, J. Am. Chem. Soc., 2010, 132, 17817.CrossRefGoogle Scholar
  19. 19.
    T. S. Cameron, A. Decken, F. Grein, C. Knapp, J. Passmore, J. M. Rautiainen, K. V. Shuvaev, R. C. Thompson, D. J. Wood, Inorg. Chem., 2010, 49, 7861.CrossRefGoogle Scholar
  20. 20.
    M. Deumal, J. M. Rawson, J. A. K. Howard, R. C. B. Copley, M. A. Robb, J. J. Novoa, Chem. Eur. J., 2010, 16, 2741.CrossRefGoogle Scholar
  21. 21.
    J. M. Rawson, A. Alberola, in Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium, Ed. F. Devillanova, RSC Press, Cambridge, 2007.Google Scholar
  22. 22.
    K. E. Preuss, Dalton Trans., 2007, 2357.Google Scholar
  23. 23.
    K. Awaga, T. Tanaka, T. Shirai, Y. Umezono, W. Fujita, C. R. Chim., 2007, 10, 52.CrossRefGoogle Scholar
  24. 24.
    M. Deumal, S. LeRoux, J. M. Rawson, M. A. Robb, J. J. Novoa, Polyhedron, 2007, 26, 1949.CrossRefGoogle Scholar
  25. 25.
    J. M. Rawson, A. Alberola, A. Whalley, J. Mater. Chem., 2006, 16, 2560.CrossRefGoogle Scholar
  26. 26.
    J. M. Rawson, P. Luzon, F. Palacio, Coord. Chem. Rev., 2005, 249, 2631.CrossRefGoogle Scholar
  27. 27.
    J. M. Rawson, F. Palacio, Struct. Bonding, 2001, 100, 93.CrossRefGoogle Scholar
  28. 28.
    J. M. Rawson, G. D. McManus, Coord. Chem. Rev., 1999, 189, 135.CrossRefGoogle Scholar
  29. 29.
    Z. V. Todres, Ion-Radical Organic Chemistry: Principles and Applications, CRC Press, Boca Raton, 2009.Google Scholar
  30. 30.
    P. Hanson, Adv. Heterocycl. Chem., 1980, 27, 31.CrossRefGoogle Scholar
  31. 31.
    C. L. Kwan, M. Carmack, J. K. Kochi, J. Phys. Chem., 1976, 80, 1786.CrossRefGoogle Scholar
  32. 32.
    M. Kamiya, Y. Akahori, Bull. Chem. Soc. Jpn, 1970, 43, 268.CrossRefGoogle Scholar
  33. 33.
    N. M. Atherton, J. N. Ockwell, R. Dietz, J. Chem. Soc. A, 1967, 771.Google Scholar
  34. 34.
    H. Bock, P. Haenel, R. Neidlein, Phosphorus, Sulfur, Relat. Elem., 1988, 39, 235.CrossRefGoogle Scholar
  35. 35.
    A. V. Zibarev, R. Mews, in Selenium and Tellurium Chemistry: From Small Molecules to Biomolecules and Materials, Eds J. D. Woollins, R. S. Laitinen, Springer, Heidelberg, 2011, 123.Google Scholar
  36. 36.
    A. Yu. Makarov, I. G. Irtegova, N. V. Vasilieva, I. Yu. Bagryanskaya, T. Borrmann, Yu. V. Gatilov, E. Lork, R. Mews, W.-D. Stohrer, A. V. Zibarev, Inorg. Chem., 2005, 44, 7194.CrossRefGoogle Scholar
  37. 37.
    V. N. Ikorskii, I. G. Irtegova, E. Lork, A. Yu. Makarov, R. Mews, V. I. Ovcharenko, A. V. Zibarev, Eur. J. Inorg. Chem., 2006, 3061.Google Scholar
  38. 38.
    I. Yu. Bagryanskaya, Yu. V. Gatilov, N. P. Gritsan, N. V. Ikorskii, I. G. Irtegova, A. V. Lonchakov, E. Lork, R. Mews, V. I. Ovcharenko, N. A. Semenov, N. V. Vasilieva, A. V. Zibarev, Eur. J. Inorg. Chem., 2007, 4751.Google Scholar
  39. 39.
    N. P. Gritsan, A. V. Lonchakov, E. Lork, R. Mews, E. A. Pritchina, A. V. Zibarev, Eur. J. Inorg. Chem., 2008, 1994.Google Scholar
  40. 40.
    S. N. Konchenko, N. P. Gritsan, A. V. Lonchakov, I. G. Irtegova, R. Mews, V. I. Ovcharenko, U. Radius, A. V. Zibarev, Eur. J. Inorg. Chem., 2008, 3833.Google Scholar
  41. 41.
    N. A. Semenov, N. A. Pushkarevsky, A. V. Lonchakov, A. S. Bogomyakov, E. A. Pritchina, E. A. Suturina, N. P. Gritsan, S. N. Konchenko, R. Mews, V. I. Ovcharenko, A. V. Zibarev, Inorg. Chem., 2010, 49, 7558.CrossRefGoogle Scholar
  42. 42.
    S. N. Konchenko, N. P. Gritsan, A. V. Lonchakov, U. Radius, A. V. Zibarev, Mendeleev Commun., 2009, 19, 7.CrossRefGoogle Scholar
  43. 43.
    E. A. Suturina, N. A. Semenov, A. V. Lonchakov, I. Yu. Bagryanskaya, Yu. V. Gatilov, I. G. Irtegova, N. V. Vasilieva, E. Lork, R. Mews, N. P. Gritsan, A. V. Zibarev, J. Phys. Chem. A, 2011, 115, 4851.CrossRefGoogle Scholar
  44. 44.
    S. P. Solodovnikov, Usp. Khim., 1982, 51, 1674 [Russ. Chem. Rev. (Engl. Transl.), 1982, 51].Google Scholar
  45. 45.
    V. D. Shteingarts, L. S. Kobrina, I. I. Bil’kis, V. F. Starichenko, Khimiya poliftorarenov: mekhanizmy reaktsii, intermediaty [Chemistry of Polyfluoroarenes: Reaction Mechanisms and Intermediates], Nauka, Novosibirsk, 1991, 272 pp. (in Russian).Google Scholar
  46. 46.
    N. V. Vasilieva, I. G. Irtegova, N. P. Gritsan, A. V. Lonchakov, A. Yu. Makarov, L. A. Shundrin, A. V. Zibarev, J. Phys. Org. Chem., 2010, 23, 536.CrossRefGoogle Scholar
  47. 47.
    E. Lork, R. Mews, A. V. Zibarev, Mendeleev Commun., 2009, 19, 147.CrossRefGoogle Scholar
  48. 48.
    O. Kahn, Molecular Magnetism, VCH Publishers, New York, 1993.Google Scholar
  49. 49.
    J. J. Novoa, M. Deumal, Struct. Bonding, 2001, 100, 33.CrossRefGoogle Scholar
  50. 50.
    J. C. Bonner, M. E. Fisher, Phys. Rev., 1964, 135, A640.CrossRefGoogle Scholar
  51. 51.
    W. E. Hatfield, J. Appl. Phys., 1985, 52, 1985.CrossRefGoogle Scholar
  52. 52.
    G. S. Rushbrooke, P. J. Wood, Proc. Phys. Soc. A, 1955, 68, 1161.CrossRefGoogle Scholar
  53. 53.
    G. S. Rushbrooke, P. J. Wood, Mol. Phys., 1958, 1, 257.CrossRefGoogle Scholar
  54. 54.
    C. S. Clarke, J. Jornet, M. Deumal, J. J. Novoa, Polyhedron, 2009, 28, 1614.CrossRefGoogle Scholar
  55. 55.
    P. R. Moreira, F. Illas, Phys. Chem. Chem. Phys., 2006, 8, 1645.CrossRefGoogle Scholar
  56. 56.
    L. Noodleman, D. A. Case, J. M. Mouesca, Coord. Chem. Rev., 1995, 144, 199.CrossRefGoogle Scholar
  57. 57.
    J. S. Morgan, M. Jennings, A. Vindigni, R. Clerac, K. E. Preuss, Cryst. Growth Des., 2011, 11, 2520.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  1. 1.Institute of Chemical Kinetics and CombustionSiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation
  2. 2.Department of PhysicsNovosibirsk State UniversityNovosibirskRussian Federation
  3. 3.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation

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