Russian Journal of General Chemistry

, Volume 85, Issue 10, pp 2338–2347 | Cite as

Chemical and electrochemical synthesis, local atomic structure, and properties of copper(II), cobalt(II), and nickel(II) complexes with azo compounds containing an additional azo group in the para or ortho position of the amine fragment

  • A. S. Burlov
  • S. A. Mashchenko
  • V. G. Vlasenko
  • E. D. Garnovskaya
  • Ya. V. Zubavichus
  • S. I. Levchenkov
  • Yu. S. Kurinnaya
Article

Abstract

New copper(II), cobalt(II), and nickel(II) complexes with 1-[4-(phenydiazenyl)phenyldiazenyl]-naphthalen-2-ol and 1-[4-methyl-2-(4-methylphenyldiazenyl)phenyldiazenyl]naphthalen-2-ol have been synthesized by chemical and electrochemical methods and characterized by IR, 1H NMR, and X-ray absorption spectroscopy, as well as by magnetochemistry and quantum chemical calculations. Coordination of the nitrogen atom in the additional azo group to the metal ion is determined by its position (ortho or para) and metal nature.

Keywords

azo compounds metal chelates X-ray absorption spectroscopy local atomic structure magnetochemistry quantum chemical calculations 

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References

  1. 1.
    Comprehensive Coordination Chemistry II, McCleverty, Y.A. and Meyer, T.J., Eds., Amsterdam: Elsevier, 2004.Google Scholar
  2. 2.
    Bhunia, P., Sardar, D., Sarker, K.K., Ray, U.S., Ray, J.-S., Wu, J.S., Lu, T.-H., and Sinha, C., J. Coord. Chem., 2009, vol. 62, p. 552. DOI: 10.1080/00958970802291282.CrossRefGoogle Scholar
  3. 3.
    Nandi, S., Bannerjee, D., Wu, J.-S., Lu, T.-H., Slawin, A.M.Z., Woolins, J.D., Ribas, J., and Sinha, C., Eur. J. Inorg. Chem., 2009, no. 26, p. 3972. DOI: 10.1002/ejic.200900423.CrossRefGoogle Scholar
  4. 4.
    Porai-Koshits, B.A., Azokrasiteli (Azo Dyes), Leningrad: Khimiya, 1972.Google Scholar
  5. 5.
    Kondil, S.S., Transition Met. Chem., 1998, vol. 23, p. 461. DOI: 10.1023/A:1006900923122.CrossRefGoogle Scholar
  6. 6.
    Daniel, J.W., Toxicol. Appl. Pharmacol., 1962, vol. 4, p. 572.CrossRefGoogle Scholar
  7. 7.
    Broekaert, J.A. and Hörmann, P.K., Anal. Chim. Acta, 1981, vol. 124, p. 421. DOI: 10.1016/S0003-2670(01)93591-3.CrossRefGoogle Scholar
  8. 8.
    Kurtoglu, M., Birbicer, N., Kimyonsen, U., and Serin, S., Dyes Pigm., 1999, vol. 41, p. 143.CrossRefGoogle Scholar
  9. 9.
    Sato, O., Tao, J., and Zhang, Y.-Z., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2152. DOI: 10.1002/anie.200602205.CrossRefGoogle Scholar
  10. 10.
    Ire, M., Chem. Rev., 2000, vol. 100, no. 5, p. 1683. DOI: 10.1021/cr980068l.CrossRefGoogle Scholar
  11. 11.
    Delaire, J.A. and Nakatani, K., Chem. Rev., 2000, vol. 100, no. 5, p. 1817. DOI: 10.1021/cr980078m.CrossRefGoogle Scholar
  12. 12.
    Lee, S.H., Kim, S.K., Bok, J.H., Yoon, J., Lee, K., and Kim, J.S., Tetrahedron Lett., 2005, vol. 46, no. 47, p. 8163. DOI: 10.1016/jtetlet.2005.09.117.CrossRefGoogle Scholar
  13. 13.
    Sarker, K.K., Sardar, D., Suwa, K., Otsuki, J., and Sinha, C., Inorg. Chem., 2007, vol. 46, no. 20, p. 8291. DOI: 10.1021/ic7012073.CrossRefGoogle Scholar
  14. 14.
    Synthetic Coordination and Organometallic Chemistry, Garnovskii, A.D. and Kharisov, B.I., Eds., New York: Marcel Dekker, 2003.Google Scholar
  15. 15.
    Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, p. 193. DOI: 10.1070/RC2005v074n03ABEH001164.CrossRefGoogle Scholar
  16. 16.
    Kogan, V.A. and Shcherbakov, I.N., Ros. Khim. Zh., 2004, vol. 48, no. 1, p. 69.Google Scholar
  17. 17.
    Burlov, A.S., Nikolaevskii, S.A., Vasil’chenko, 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
  18. 18.
    Garnovskii, A.D., Burlov, A.S., Metelitsa, A.V., Vasil’chenko, 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.CrossRefGoogle Scholar
  19. 19.
    Gütlich, P., Garcia, Y., and Wolke, T., Coord. Chem. Rev., 2001, vols. 219–221, p. 839. DOI: 10.1016/S0010- 8545(01)00381-2.CrossRefGoogle Scholar
  20. 20.
    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
  21. 21.
    Weber, B., Coord. Chem. Rev., 2009, vol. 253, p. 2432. DOI: 10.1016/jccr.2008.10.002.CrossRefGoogle Scholar
  22. 22.
    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/S0132344X13120013.CrossRefGoogle Scholar
  23. 23.
    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/jmolstruc.2013.12.007.CrossRefGoogle Scholar
  24. 24.
    Yamamoto, T., X-Ray Spectrom., 2008, vol. 37, p. 572. DOI: 10.1002/xrs.1103.CrossRefGoogle Scholar
  25. 25.
    Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Y.V., Nucl. Instrum. Methods Phys. Res., Sect. A, 2009, vol. 603, p. 95. DOI: 10.1016/jnima.2008.12.167.CrossRefGoogle Scholar
  26. 26.
    Kochubey, 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.K., Khel’mer, B.Yu., and Shuvaev, A.T., Rentgenospektral’nyi metod izucheniya struktury amorfnykh tel: EXAFS-spektroskopiya (X-Ray Spectroscopy for Studying the Structure of Amorphous Materials: EXAFS Spectroscopy), novosibirsk: Nauka, Sib. Otd., 1988.Google Scholar
  27. 27.
    Newville, M., J. Synchrotron Radiat., 2001, vol. 8, p. 96. DOI: 10.1107/S0909049500016290.CrossRefGoogle Scholar
  28. 28.
    Zabinski, S.I., Rehr, J.J., Ankudinov, A., and Alber, R.C., Phys. Rev. B, 1995, vol. 52, p. 2995. DOI: 10.1103/PhysRevB.52.2995.CrossRefGoogle Scholar
  29. 29.
    Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58, p. 380. DOI: 10.1107/S0108768102003890.CrossRefGoogle Scholar
  30. 30.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision C 02, Wallingford CT: Gaussian, 2004.Google Scholar
  31. 31.
    Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, p. 785. DOI: 10.1103/PhysRevB.37.785.CrossRefGoogle Scholar
  32. 32.
    Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. DOI: 10.1063/1.464913.CrossRefGoogle Scholar
  33. 33.
    Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, no. 2, p. 724. DOI: 10.1063/1.1674902.CrossRefGoogle Scholar
  34. 34.
    Nivorozhkin, A.L., Toftlund, H., Nivorozhkin, L.E., Kamenetskaya, I.A., Antsishkina, A.S., and Porai-Koshits, M.A., Transition Met. Chem., 1994, vol. 19, no. 3, p. 319. DOI: 10.1007/BF00139103.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • A. S. Burlov
    • 1
  • S. A. Mashchenko
    • 1
  • V. G. Vlasenko
    • 2
  • E. D. Garnovskaya
    • 1
  • Ya. V. Zubavichus
    • 3
  • S. I. Levchenkov
    • 4
  • Yu. S. Kurinnaya
    • 1
  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.“Kurchatov Institute” National Research CenterMoscowRussia
  4. 4.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia

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