Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 2, pp 262–270 | Cite as

Chemical and Electrochemical Synthesis, Structure, and Properties of Metal Chelates of Tridentate N,S-Containing Azomethinazo Ligands

  • A. S. Burlov
  • S. A. Mashchenko
  • V. G. Vlasenko
  • S. A. Nikolaevskii
  • M. A. Kiskin
  • Ya. V. Zubavichus
  • A. I. Uraev
  • D. A. Garnovskii
  • E. V. Korshunova
  • S. I. Levchenkov
Article
  • 23 Downloads

Abstract

Novel Cu(II), Co(II), Ni(II), and Zn(II) complexes of 5-methyl-2-phenyl-4-[(4-phenylazo)anilinemethylylidene]- 2,4-dihydro-3H-pyrazole-3-thione and 5-methyl-4-[4-methyl-2-(4-methylphenylazo)anilinemethylylidene]- 2-phenyl-2,4-dihydro-3H-pyrazole-3-thione, i.e. ligands containing the phenylazo group in the ortho and para positions of the aniline fragment, were synthesized by the chemical and electrochemical methods. The complexes and ligands were characterized by IR, 1H NMR, X-ray absorption spectroscopy and magnetochemistry. The azo group of the ligands is not involved in coordination to the metal.

Keywords

azomethines metal chelates X-ray absorption spectroscopy local atomic structure magnetochemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Hernandez Molina, R. and Mederos, A., Comprehensive Coordination Chemistry II, Lever, A.B.P., Ed., Amsterdam: Elsevier–Pergamon, 2003, vol. 1, p. 411.CrossRefGoogle Scholar
  2. 2.
    Synthetic Coordination and Organometallic Chemistry, Garnovskii, A.D. and Kharisov, B.I., New York: Marcel Dekker, 2003.Google Scholar
  3. 3.
    Vigato, P.A. and Tamburini, S., Coord. Chem. Rev., 2004, vol. 248, no. 17, p. 1717. doi 10.1016/j.cct.2003.09.003CrossRefGoogle Scholar
  4. 4.
    Vigato, P.A., Tamburini, S., and Bertelo, L., Coord. Chem. Rev., 2007, vol. 251, no. 11, p. 1311. doi 10.1016/j.ccr.2006.11.016CrossRefGoogle Scholar
  5. 5.
    Vigato, P.A. and Tamburini, S., Coord. Chem. Rev., 2008, vol. 252, no. 18, p. 1871. doi 10.1016/j.ccr.2007.10.030CrossRefGoogle Scholar
  6. 6.
    Garnovskii, A.D. and Vasilchenko, I.S., Russ. Chem. Rev., 2002, vol. 71, no. 11, p. 943. doi 10.1070/RC2002v071n11ABEH000759CrossRefGoogle Scholar
  7. 7.
    Garnovskii, A.D. and Vasilchenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, p. 193. doi 10.1070/RC2005v074n03ABEH001164CrossRefGoogle Scholar
  8. 8.
    Garnovskii, A.D., Vasilchenko, I.S., Garnovskii, D.A., and Kharisov, B.I., J. Coord. Chem., 2009, vol. 62, no. 2, p. 151. doi 10.1080/00958970802398178CrossRefGoogle Scholar
  9. 9.
    Garnovskii, A.D., Sadimenko, A.P., Vasilchenko, I.S., Garnovskii, D.A., Sennikova, E.V., and Minkin, V.I., Adv. Heterocycl. Chem., 2009, vol. 97, p. 291. doi 10.1016/S0065-2725(08)00205-5CrossRefGoogle Scholar
  10. 10.
    Darensbourg, D.J., Mackiewicz, R.M., Phelps, A.L., and Billodeaux, D.R., Acc. Chem. Res., 2004, vol. 37, no. 7, p. 836. doi 10.1021/ar030240uCrossRefGoogle Scholar
  11. 11.
    Miyasaka, H., Saitoh, A., and Abe, S., Coord. Chem. Rev., 2007, vol. 251, no. 21, p. 2622. doi 10.1016/j.ccr.2007.07.028CrossRefGoogle Scholar
  12. 12.
    Gupta, K.S. and Sutar, A.K., Coord. Chem. Rev., 2008, vol. 252, no. 12, p. 1420. doi 10.1016/j.ccr.2007.09.005CrossRefGoogle Scholar
  13. 13.
    Burlov, A.S., Antsyshkina, A.S., Sadikov, G.G., Divaeva, L.N., Garnovskii, A.D., and Sergienko, V.S., Russ. J. Coord. Chem., 2000, vol. 26, no. 9, p. 648.Google Scholar
  14. 14.
    Garnovskii, A.D., Vasilchenko, I.S., Garnovskii, D.A., Burlov, A.S., and Uraev, A.I., Ross. Kim. Zh., 2009, vol. 53, no. 1, p. 100.Google Scholar
  15. 15.
    Garnovskii, A.D., Ikorskii, V.N., Uraev, A.I., Vasilchenko, I.S., Burlov, A.S., Garnovskii, D.A., Lyssenko, K.A., Vlasenko, V.G., Shestakova, T.E., Koshchienko, Yu.V., Kuz’menko, T.A., Divaeva, L.N., Bubnov, M.P., Rybalkin, V.P., Korshunov, O.Yu., Pirog, I.V., Borodkin, G.S., Bren, V.A., Uflyand, I.E., Antipin, M.Yu., and Minkin, V.I., J. Coord. Chem., 2007, vol. 60, no. 4, p. 1493. doi 10.1080/00958970601080365CrossRefGoogle Scholar
  16. 16.
    Burlov, A.S., Nikolaevskii, S.A., Vasilchenko, I.S., Koshchienko, Y.V., Uraev, A.I., Sennikova, E.V., Borodkin, G.S., Garnovskii, A.D., Minkin, V.I., Bogomyakov, A.S., Vlasenko, V.G., and Garnovskii, D.A., Russ. J. Coord. Chem., 2009, vol. 35, no. 7, p. 486.CrossRefGoogle Scholar
  17. 17.
    Li, X.-M., Wang, C.-F., Zuo, J.-L., and You, X.-Z., J. Coord. Chem., 2009, vol. 62, no. 9, p. 1544. doi 10.1080/00958970802669222CrossRefGoogle Scholar
  18. 18.
    Metelitsa, A.V., Burlov, A.S., Bezugly, S.O., Borodkina, I.G., Bren, V.A., Garnovskii, A.D., and Minkin, V.I., Russ. J. Coord. Chem., 2006, vol. 32, no. 12, p. 858. doi 10.1134/S1070328406120025CrossRefGoogle Scholar
  19. 19.
    Zhang, L., Jiang, F., and Zhou, Yu., J. Coord. Chem., 2009, vol. 62, no. 9, p. 1476. doi 10.1080/00958970802596383CrossRefGoogle Scholar
  20. 20.
    Holm, R.H. and Solomon, E.I., Chem. Rev., 2004, vol. 104, no. 2, p. 347. doi 10.1021/cr0206364CrossRefGoogle Scholar
  21. 21.
    Elmali, F.T., Peksel, A., and Demirhan, N.J., Coord. Chem., 2009, vol. 62, no. 15, p. 2548. doi 10.1080/00958970902842471CrossRefGoogle Scholar
  22. 22.
    Ahmadi, R.A. and Amani, S., Molecules, 2012, vol. 17, no. 6, p. 6434. doi 10.3390/molecules/17066434CrossRefGoogle Scholar
  23. 23.
    Sarigul, M., Deveci, P., Kose, M., Arslan, U., Dagi, H.T., and Kurtoglu, M., J. Mol. Struct., 2015, vol. 1096, p. 64. doi 10.1016/j.molstruc.2015.04.043CrossRefGoogle Scholar
  24. 24.
    Chigarenko, G.G., Ponomarenko, A.G., Bolotnikov, V.S., Alekseev, V.A., Burlov, A.S., Garnovskii, A.D., and Barchan, G.P., Trenie Iznos., 1989, vol. 10, no. 6, p. 1050.Google Scholar
  25. 25.
    Barchan, G.P., Chigarenko, G.G., Kogan, V.A., Burlov, A.S., and Bolotnikov, V.S., USSR Inventor’s Certificate no. 810778; Byull. Izobret., 1981, no. 9.Google Scholar
  26. 26.
    Barchan, G.P., Chigarenko, G.G., Burlov, A.S., Kogan, V.A., Bulgarevich, A.S., and Bulgarevich, S.B., USSR Inventor’s Certificate 910741, Byull. Izobret., 1982, no. 9.Google Scholar
  27. 27.
    Garnovskii, A.D., Burlov, A.S., Metelitsa, A.V., Vasilchenko, I.S., Nikolaevskii, S.A., Borodkina, I.G., Minkin, V.I., Starikov, A.G., and Bezugliy, S.O., Russ. J. Coord. Chem., 2010, vol. 36, no. 7, p. 479. doi 10.1134/S1070328410070018CrossRefGoogle Scholar
  28. 28.
    Gütlich, P., Garcia, Y., and Wolke, T., Coord. Chem. Rev., 2001, vol. 219, p. 839. doi 10.1016/S0010-8545 (01)00381-2CrossRefGoogle Scholar
  29. 29.
    Wang, P., Ming, H., Zhang, J.Y., Liang, Z.C., Lu, Y.H., Zhang, Q.J., Xie, J.P., and Tian, Y.P., Opt. Commun., 2002, vol. 203, p. 159. doi 10.1016/S0030-4018(02) 01098-2CrossRefGoogle Scholar
  30. 30.
    Weber, B., Coord. Chem. Rev., 2009, vol. 253, p. 2432. doi 10.1016/j.ccr.2008.10.002CrossRefGoogle Scholar
  31. 31.
    Burlov, A.S., Mashchenko, S.A., Nikolaevskii, S.A., Uraev, A.I., Korshunova, E.V., Antsyshkina, A.S., Sadikov, G.G., Sergienko, V.S., Kiskin, M.A., Vlasenko, V.G., Zubavichus, Ya.V., Garnovskii, D.A., and Levchenkov, S.I., Russ. J. Coord. Chem., 2013, vol. 39, no. 12, p. 813. doi 10.7868/S0132344X13120013CrossRefGoogle Scholar
  32. 32.
    Burlov, A.S., Mashchenko, S.A., Vlasenko, V.G., Zubavichus, Y.V., Uraev, A.I., Lyssenko, K.A., Levchenkov, S.I., Vasilchenko, I.S., Garnovskii, D.A., and Borodkin, G.S., J. Mol. Struct., 2014, vol. 1061, p. 47. doi 10.1016/j.molstruc.2013.12.007CrossRefGoogle Scholar
  33. 33.(a)
    Kurkovskaya, L.N., Shapet’ko, N.I., Kvitko, I.Ya., Koshelev, Yu.N., and Samartseva, E.D., Zh. Org. Khim., 1974, vol. 10, no. 10, p. 2210.Google Scholar
  34. (b).
    Kurkovskaya, L.N, Shapet’ko, N.N., and Kvitko, I.Ya., Zh. Org. Khim, 1973, vol. 9, no. 4, p. 821.Google Scholar
  35. 34.
    Antsyshkina, A.S., Sadikov, G.G., Uraev, A.I., Korshunov, O.Yu., Nivorozhkin, A.L., and Garnovskii, A.D., Crystallogr. Rep., 2000, vol. 45, no. 5, p. 778. doi 10.1134/1.1312919CrossRefGoogle Scholar
  36. 35.
    Burlov, A.S., Uraev, A.I., Garnovskii, D.A., Lyssenko, K.A., Vlasenko, V.G., Zubavichus, Y.V., Murzin, V.Y., Korshunova, E.V., Borodkin, G.S., Levchenkov, S.I., Vasilchenko, I.S., and Minkin, V.I., J. Mol. Stuct., 2014, vol. 1064, p. 111. doi 10.1016/j.molstruc.2014.02.019CrossRefGoogle Scholar
  37. 36.
    Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc. Perkin Trans. 2, 1987, p. 1.Google Scholar
  38. 37.
    Rakitin, Yu.V. and Kalinnikov, V.T., Sovremennaya magnetokhimiya (Modern Magnetochemistry), St. Petersburg: Nauka, 1994.Google Scholar
  39. 38.
    Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Y.V., Nucl. Instr. Meth. Phys. Res. A, 2009, vol. 603, p. 95. doi 10.1016/j.nima.2008.12.16CrossRefGoogle Scholar
  40. 39.
    Kochubei, D.I., Babanov, Yu.A., Zamaraev, K.I., Vedrinskii, R.V., Kraizman, V.L., Kulipanov, G.N., Mazalov, L.N., Skrinskii, A.N., Fedorov, V.I., Khel’mer, B.Yu., and Shuvaev, A.T., Rentgenospektral’nyi metod izucheniya struktury amorfnykh tel: EXAFS-spektroskopiya (X-ray Spectral Method of Studying the Structure of Amorphous Substances: EXAFS Spectroscopy), Novosibirsk: Nauka. Sib. Otd., 1988.Google Scholar
  41. 40.
    Newville, M., J. Synchrotron Rad., 2001, no. 8, p. 96. doi 10.1107/S0909049500016290CrossRefGoogle Scholar
  42. 41.
    Zabinsky, S.I., Rehr, J.J., Ankudinov, A., Albers, R.C., and Eller, M.J., Phys. Rev. B, 1995, vol. 52, p. 2995. doi 10.1103/PhysRevB. 52.2995CrossRefGoogle Scholar
  43. 42.
    SMART (Control) and SAINT (Integration) Software, Version 5.0. Madison, Wis., USA: Bruker AXS, 1997.Google Scholar
  44. 43.
    Sheldrick, G.M., SADABS, Program for Scanning and Correction of Area Detector Data, Göttingen, Germany: Göttinngen Univ., 2003.Google Scholar
  45. 44.
    Sheldrik, G.M., Acta Crystallogr. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930CrossRefGoogle Scholar
  46. 45.
    Kvitko, I.Ya. and Poray-Koshits, B.A., Zh. Org. Khim., 1969, vol. 5, no. 9, p. 1685.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • A. S. Burlov
    • 1
  • S. A. Mashchenko
    • 1
  • V. G. Vlasenko
    • 2
  • S. A. Nikolaevskii
    • 3
  • M. A. Kiskin
    • 3
  • Ya. V. Zubavichus
    • 4
  • A. I. Uraev
    • 1
  • D. A. Garnovskii
    • 5
  • E. V. Korshunova
    • 1
  • S. I. Levchenkov
    • 5
  1. 1.Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia
  2. 2.Research Institute of PhysicsSouthern Federal UniversityRostov-on-DonRussia
  3. 3.Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussia
  4. 4.Kurchatov Institute National Research CenterMoscowRussia
  5. 5.Southern Research CenterRussian Academy of SciencesRostov-on-DonRussia

Personalised recommendations