Skip to main content
Log in

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

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Comprehensive Coordination Chemistry II, McCleverty, Y.A. and Meyer, T.J., Eds., Amsterdam: Elsevier, 2004.

  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.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  4. Porai-Koshits, B.A., Azokrasiteli (Azo Dyes), Leningrad: Khimiya, 1972.

    Google Scholar 

  5. Kondil, S.S., Transition Met. Chem., 1998, vol. 23, p. 461. DOI: 10.1023/A:1006900923122.

    Article  Google Scholar 

  6. Daniel, J.W., Toxicol. Appl. Pharmacol., 1962, vol. 4, p. 572.

    Article  CAS  Google Scholar 

  7. Broekaert, J.A. and Hörmann, P.K., Anal. Chim. Acta, 1981, vol. 124, p. 421. DOI: 10.1016/S0003-2670(01)93591-3.

    Article  CAS  Google Scholar 

  8. Kurtoglu, M., Birbicer, N., Kimyonsen, U., and Serin, S., Dyes Pigm., 1999, vol. 41, p. 143.

    Article  CAS  Google Scholar 

  9. Sato, O., Tao, J., and Zhang, Y.-Z., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2152. DOI: 10.1002/anie.200602205.

    Article  CAS  Google Scholar 

  10. Ire, M., Chem. Rev., 2000, vol. 100, no. 5, p. 1683. DOI: 10.1021/cr980068l.

    Article  Google Scholar 

  11. Delaire, J.A. and Nakatani, K., Chem. Rev., 2000, vol. 100, no. 5, p. 1817. DOI: 10.1021/cr980078m.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  14. Synthetic Coordination and Organometallic Chemistry, Garnovskii, A.D. and Kharisov, B.I., Eds., New York: Marcel Dekker, 2003.

  15. Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, p. 193. DOI: 10.1070/RC2005v074n03ABEH001164.

    Article  CAS  Google Scholar 

  16. Kogan, V.A. and Shcherbakov, I.N., Ros. Khim. Zh., 2004, vol. 48, no. 1, p. 69.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  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) 01098-2

    Article  CAS  Google Scholar 

  21. Weber, B., Coord. Chem. Rev., 2009, vol. 253, p. 2432. DOI: 10.1016/jccr.2008.10.002.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  24. Yamamoto, T., X-Ray Spectrom., 2008, vol. 37, p. 572. DOI: 10.1002/xrs.1103.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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. Newville, M., J. Synchrotron Radiat., 2001, vol. 8, p. 96. DOI: 10.1107/S0909049500016290.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  29. Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58, p. 380. DOI: 10.1107/S0108768102003890.

    Article  Google Scholar 

  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. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, p. 785. DOI: 10.1103/PhysRevB.37.785.

    Article  CAS  Google Scholar 

  32. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. DOI: 10.1063/1.464913.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. S. Burlov.

Additional information

Original Russian Text © A.S. Burlov, S.A. Mashchenko, V.G. Vlasenko, E.D. Garnovskaya, Ya.V. Zubavichus, S.I. Levchenkov, Yu.S. Kurinnaya, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 10, pp. 1708–1717.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Burlov, A.S., Mashchenko, S.A., Vlasenko, V.G. et al. 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. Russ J Gen Chem 85, 2338–2347 (2015). https://doi.org/10.1134/S1070363215100199

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215100199

Keywords

Navigation