Skip to main content
SpringerLink
Log in

Effect of an additional functional group on the structure and properties of copper(II) and nickel(II) o-iminoquinone complexes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Nickel(II) and copper(II) bis-o-iminosemiquinone complexes were synthesized based on 4,6-di-tert-butyl-N-(2-methoxyphenyl)-o-aminophenol (Ni(imSQOMe)2 (1) and Cu(imSQOMe)2 (2)), and methyl 2-(3,5-di-tert-butyl-2-hydroxyphenylamino)benzoate (Ni(imSQC(O)OMe)2 (3) and Cu(imSQC(O)OMe)2 (4)). The molecular structures of these complexes were established by X-ray diffraction. The metal atoms in complexes 1, 3, and 4 are in square-planar coordination, whereas the square-planar coordination of the copper atom in complex 2 is substantially distorted, as evidenced by the angle between the planes of the o-iminosemiquinone ligands (22.7°). Complexes 1 and 3 are diamagnetic. The absence of line broadening in the 1H NMR spectra of these compounds at 293 K attests to the singlet spin state. The temperature dependences of the effective magnetic moment for complexes 2 and 4 are indicative of their doublet ground spin state (S = 1/2) and the thermally populated quartet state (S = 3/2). The presence of an unpaired electron on the metal center in the ground spin state for compounds 2 and 4 was confirmed by EPR spectroscopy.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. C. G. Pierpont, Coord. Chem. Rev., 2001, 216–217, 99.

    Article  Google Scholar 

  2. C. G. Pierpont, Coord. Chem. Rev., 2001, 219–221, 415.

    Article  Google Scholar 

  3. A. I. Poddel´sky, V. K. Cherkasov, G. A. Abakumov, Coord. Chem. Rev., 2009, 253, 291.

    Article  Google Scholar 

  4. O. Sato, J. Tao, Y.-Zh. Zhang, Angew. Chem., Int. Ed., 2007, 46, 2152.

    Article  CAS  Google Scholar 

  5. A. Dei, D. Gatteschi, C. Sangregorio, L. Sorace, Acc. Chem. Res., 2004, 37, 827.

    Article  CAS  Google Scholar 

  6. P. J. Chirik, K. Wieghardt, Science, 2010, 327, 794.

    Article  CAS  Google Scholar 

  7. W. Kaim, B. Schwederski, Coord. Chem. Rev., 2010, 254, 1580.

    Article  CAS  Google Scholar 

  8. V. Lyaskovskyy, B. de Bruin, AC Catal., 2012, 2, 270.

    Article  CAS  Google Scholar 

  9. V. I. Ovcharenko, E. V. Gorelik, S. V. Fokin, G. V. Romanenko, V. N. Ikorskii, A. V. Krashilina, V. K. Cherkasov, G. A. Abakumov, J. Am. Chem. Soc., 2007, 129, 10512.

    Article  CAS  Google Scholar 

  10. Sh. Ye, B. Sarkar, F. Lissner, Th. Schleid, J. Slageren, J. Fiedler, W. Kaim, Angew. Chem., Int. Ed., 2005, 44, 2103.

    Article  CAS  Google Scholar 

  11. P. Chaudhuri, C. N. Verani, E. Bill, E. Bothe, T. Weyhermuller, K. Wieghardt, J. Am. Chem. Soc., 2001, 123, 2213.

    Article  CAS  Google Scholar 

  12. R. Rakshit, S. Ghorai, S. Biswas, C. Mukherjee, Inorg. Chem., 2014, 53, 3333.

    Article  CAS  Google Scholar 

  13. W. Kaim, Inorg. Chem., 2011, 50, 9752.

    Article  CAS  Google Scholar 

  14. S. E. Balaghi, E. Safaei, L. Chiang, E. W. Y. Wong, D. Savard, R. M. Clarke, T. Storr, Dalton Trans., 2013, 42, 6829.

    Article  CAS  Google Scholar 

  15. C. Mukherjee, T. Weyhermuller, E. Bothe, P. Chaudhuri, Inorg. Chem., 2008, 47, 11620.

    Article  CAS  Google Scholar 

  16. A. Mukherjee, R. Mukherjee, Ind. J. Chem., Sect. A, 2011, 50, 484.

    Google Scholar 

  17. E. Bill, E. Bothe, P. Chaudhuri, K. Chlopek, D. Herebian, S. Kokatam, K. Ray, T. Weyhermuller, F. Neese, K. Wieghardt, Chem. Eur. J., 2005, 11, 204.

    Article  Google Scholar 

  18. S. N. Brown, Inorg. Chem., 2012, 51, 1251.

    Article  CAS  Google Scholar 

  19. D. Herebian, K. E. Wieghardt, F. Neese, J. Am. Chem. Soc., 2003, 125, 10997.

    Article  CAS  Google Scholar 

  20. A. Paretzki, M. Bubrin, J. Fiedler, S. Zalis, W. Kaim, Chem. Eur. J., 2014, 20, 5414.

    Article  CAS  Google Scholar 

  21. S. S. Batsanov, Russ. J. Inorg. Chem. (Engl. Transl.), 1991, 36, 1694 [Zh. Neorg. Khim., 1991, 36, 3015].

    Google Scholar 

  22. S. Mukherjee, E. Rentschler, T. Weyhermuller, K. Wieghardt, P. Chaudhuri, Chem. Commun., 2003, 1828.

    Google Scholar 

  23. C. Mukherjee, T. Weyhermuller, E. Bothe, P. Chaudhuri, Inorg. Chem., 2008, 47, 2740.

    Article  CAS  Google Scholar 

  24. C. Mukherjee, U. Pieper, E. Bothe, V. Bachler, E. Bill, T. Weyhermuller, P. Chaudhuri, Inorg. Chem., 2008, 47, 8943.

    Article  CAS  Google Scholar 

  25. C. Mukherjee, T. Weyhermuller, E. Bothe, E. Rentschler, P. Chaudhuri, Inorg. Chem., 2007, 46, 9895.

    Article  CAS  Google Scholar 

  26. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1988, 534 p.

    Google Scholar 

  27. A. J. Gordon, R. A. Ford, The Chemist´s Companion, Wiley Intersci. Publ., New York, 1972, 537 p.

    Google Scholar 

  28. S. Ghorai, C. Mukherjee, Chem. Commun., 2012, 48, 10180.

    Article  CAS  Google Scholar 

  29. Zyong Ngia Banga, V. N. Komissarov, Yu. A. Sayapin, V. V. Tkachev, G. V. Shilov, S. M. Aldoshin, V. I. Minkin, Russ. J. Org. Chem. (Engl. Transl.), 2009, 45, 442 [Zh. Org. Khim., 2009, 45, 452].

    Article  Google Scholar 

  30. G. M. Sheldrick, SHELXTL v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.

    Google Scholar 

  31. SCALE3 ABSPACK: Empirical Absorption Correction, CrysAlis Pro — Software Package, Agilent Technologies, 2012.

  32. G. M. Sheldrick, SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 1998.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    A. V. Piskunov, I. V. Ershova, K. I. Pashanova, G. K. Fukin & V. K. Cherkasov

  2. N. I. Lobachevsky Nizhny Novgorod State University, 23 prosp. Gagarina, 603950, Nizhny Novgorod, Russian Federation

    A. V. Piskunov, M. V. Gulenova, G. K. Fukin & V. K. Cherkasov

  3. International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a ul. Institutskaya, 630090, Novosibirsk, Russian Federation

    A. S. Bogomyakov

  4. Southern Scientific Center, Russian Academy of Sciences, 16 ul. Tatishcheva, 414025, Astrakhan, Russian Federation

    I. V. Smolyaninov

Authors
  1. A. V. Piskunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Ershova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. V. Gulenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. I. Pashanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. S. Bogomyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. V. Smolyaninov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. K. Fukin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. K. Cherkasov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Piskunov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0642—0649, March, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Piskunov, A.V., Ershova, I.V., Gulenova, M.V. et al. Effect of an additional functional group on the structure and properties of copper(II) and nickel(II) o-iminoquinone complexes. Russ Chem Bull 64, 642–649 (2015). https://doi.org/10.1007/s11172-015-0912-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0912-8

Key words

Search

Navigation