Skip to main content
SpringerLink
Log in

Synthesis and DFT studies of structural and some spectral parameters of nickel(II) complex with 2-(2-hydroxybenzoyl)-N-(1-adamantyl) hydrazine carbothioamide

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

An efficient synthesis of the novel 2-(2-hydroxybenzoyl)-N-(1-adamantyl) hydrazine carbothioamide and its Ni(II) complex are described. Quantum chemical calculations including molecular geometry and vibrational frequencies were carried out for the structures to explain stability and geometry using both density functional (DFT/B3LYP) with 6-311+G(d,p) and LANL2DZ basis sets. 1H-NMR chemical shifts were also studied using a gauge-including atomic orbital approach (GIAO), and were found to be in good agreement with the experimental values. The Mulliken charges and HOMO–LUMO orbital energies were calculated and analyzed. The calculated HOMO–LUMO energies show that the charge transfer occurs within the molecule. The maximum positive atomic charge was obtained for C11 and the presence of a large negative charge on O (46) and O (45) for the ligand suggested the bonding of the Ni(II) ion with oxygen atoms. The chemical structures of the compounds were established by elemental analysis, FT-IR, 1H-NMR, 13C-NMR, UV–Vis spectra, magnetic moments, and thermal analyses. The electronic spectra and magnetic measurement studies revealed that the structure of complex is octahedral. Additionally, the cytotoxic effects of the obtained ligand and its complex were determined by using PC3 prostate cancer cell cultures. The results indicated that the ligand showed distinctly better activity than the complex.

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

Schema 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. M.S. Refat, N.M. El-Metwaly, Spectrochim. Acta Part A 92, 336–346 (2012)

    Article  CAS  Google Scholar 

  2. N.K. Singh, A. Srivastava, Trans. Met. Chem. 25, 133 (2000)

    Article  CAS  Google Scholar 

  3. V. Sharma, R. Bohra, J.E. Drake, M.B. Hursthouse, M.E. Light, Inorg. Chim. Acta 360, 2009 (2007)

    Article  CAS  Google Scholar 

  4. A.A. El-Asmy, O.A. Al-Gammal, D.A. Saad, S.E. Ghazy, J. Mol. Struct. 934, 9–22 (2009)

    Article  CAS  Google Scholar 

  5. S.A. Patil, S.N. Unki, A.D. Kulkarni, V.H. Naik, P.S. Badami, Spectrochim. Acta Part A 79, 1128–1136 (2011)

    Article  CAS  Google Scholar 

  6. M.A. Baseer, V.D. Jadhav, R.M. Phule, Y.V. Archana, Y.B. Vibhute, Orient. J. Chem. 16, 553–556 (2000)

    CAS  Google Scholar 

  7. M.P. Sathisha, U.N. Shetti, V.K. Revankar, K.S.R. Pai, Eur. J. Med. Chem. 43, 2338–2346 (2008)

    Article  CAS  Google Scholar 

  8. M.X. Li, L.Z. Zhang, D. Zhang, B.S. Ji, J.W. Zhao, Eur. J. Med. Chem. 46, 4383–4390 (2011)

    Article  CAS  Google Scholar 

  9. K.M. Vyas, R.G. Joshi, R.N. Jadeja, C.R. Prabha, V.K. Gupta, Spectrochim. Acta A 84, 256–268 (2011)

    Article  CAS  Google Scholar 

  10. E. Franco, E. Lopez-Trorres, M.A. Mendiola, M.T. Sevilla, Polyhedron 19, 441–451 (2000)

    Article  CAS  Google Scholar 

  11. M.M. Hamada, A.M. Shallaby, O. El-Shafai, A.A. El-Asmy, Transition Met. Chem. 31, 522–529 (2006)

    Article  CAS  Google Scholar 

  12. M.M. Hamada, O. El-Shafai, A.A. El-Asmy, Transition Met. Chem. 31, 714–719 (2006)

    Article  CAS  Google Scholar 

  13. M. Ramadan, M.M. El-Naggar, J. Inorg. Biochem. 63, 143–153 (1996)

    Article  CAS  Google Scholar 

  14. H.S. Seleem, B.A. El-Shetary, S.M.E. Khalil, M. Mostafa, M. Shebl, J. Coord. Chem. 58, 479–493 (2005)

    Article  CAS  Google Scholar 

  15. D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar, R.G. Yerande, Coord. Chem. Rev. 123, 49–71 (1993)

    Article  CAS  Google Scholar 

  16. M.A. Akl, D.S. Ismael, A.A. El-Asmy, Microchem. J. 83, 61–69 (2006)

    Article  CAS  Google Scholar 

  17. A.S. Abu-Surrah, M. Kettunen, Curr. Med. Chem. 13, 1337–1357 (2006)

    Article  CAS  Google Scholar 

  18. B. Anılanmert, in Therapeutic Organometallic Compounds, ed. by Luca Gallelli (Intech, 2012), p. 651

  19. N.K. Singh, S.B. Singh, A. Shrivastav, S.M. Singh, Proc. Indian. Acad. Sci. (Chem. Sci.) 113(L4), 257–273 (2001)

    Article  CAS  Google Scholar 

  20. S.A. Galal, K.H. Hegab, A.M. Hashem, N.S. Youssef, Eur. J. Med. Chem. 45, 5685–5889 (2010)

    Article  CAS  Google Scholar 

  21. M. Genc, E. Yılmaz, S. İlhan, Z. Karagoz, Res. Chem. Intermed. 39(7), 3011–3021 (2013)

    Article  CAS  Google Scholar 

  22. Z. Karagoz, Ph.D. thesis, Synthesis of Complexes of New Thiosemicarbazide Derivative Ligands and Investigation of Antitumor Properties, Firat University, 2012

  23. E.M. Saad, M.S. El-Shahwai, H. Saleh, A.A. El-Asmy, Transition Met. Chem. 32, 155–162 (2007)

    Article  CAS  Google Scholar 

  24. R. Kumar, S. Obrai, J. Mitra, A. Sharma, Spectrochim. Acta A 115, 244–249 (2013)

    Article  CAS  Google Scholar 

  25. A.D. Becke, J. Chem. Phys. 98, 5648–5652 (1993)

    Article  CAS  Google Scholar 

  26. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785–789 (1988)

    Article  CAS  Google Scholar 

  27. G.A. Patersson, M.A. Al-Laham, J. Chem. Phys. 94, 6081–6090 (1991)

    Article  Google Scholar 

  28. P.J. Hay, W.R. Wadt, J. Chem. Phys. 82, 270–284 (1985)

    Article  CAS  Google Scholar 

  29. W.R. Wadt, P.J. Hay, J. Chem. Phys. 82, 284–299 (1985)

    Article  CAS  Google Scholar 

  30. V.S. Krishnan, S. SampathKrishnan, S. Muthu, S. Renuga, Spectrochim. Acta A 115, 191–201 (2013)

    Article  Google Scholar 

  31. K. Jug, Z.B. Maksic, in Theoretical Model of Chemical Bonding, Part 3, ed. by Z.B. Maksic (Springer, Berlin, 1991), p. 233

  32. S. Fliszar, Charge Distributions and Chemical Effects (Springer, New York, 1983)

    Book  Google Scholar 

  33. V. Arjunan, M. Kalaivani, S. Senthilkumari, S. Mohan, Spectrochim. Acta A 115, 154–174 (2013)

    Article  CAS  Google Scholar 

  34. V.R. Dani, Tata McGraw—Hill, (Organic Spectroscopy, New Delhi, 1995)

  35. R.J. Abraham, M. Mobli, Magn. Reson. Chem. 45, 865–877 (2007)

    Article  CAS  Google Scholar 

  36. N.K. Singh, S.B. Singh, A. Shrivastav, S.M. Singh, Proc. Indian. Acad. Sci. (Chem. Sci.) 113, 257–273 (2001)

    Article  CAS  Google Scholar 

  37. N.K. Singh, S.B. Singh, Trans. Met. Chem. 26, 487–495 (2001)

    Article  CAS  Google Scholar 

  38. N.M. El-Metwally, I.M. Gabr, A.M. Shallaby, A.A. El-Asmy, J. Coord. Chem. 58, 1145–1159 (2005)

    Article  CAS  Google Scholar 

  39. N.K. Singh, S.B. Singh, Synth. React. Inorg. Met. Org. Chem. 32(1), 25–47 (2002)

    Article  CAS  Google Scholar 

  40. R.C. Aggarwal, K.K. Narang, Inorg. Chim. Acta 7, 651–652 (1973)

    Article  CAS  Google Scholar 

  41. H.N. Dogan, S. Rollas, H. Erdeniz, Il Farmaco 53, 462–467 (1998)

    Article  CAS  Google Scholar 

  42. H. Gökce, S. Bahceli, Spectrochim. Acta Part A 114, 61–73 (2013)

    Article  Google Scholar 

  43. M. Karbacak, M. Cınar, Ş. Emeç, M. Kurt, J. Raman Spectrosc. 41, 98–105 (2010)

    Article  Google Scholar 

Download references

Acknowledgments

We are indebted to the Firat University Research Foundation (FUBAP 1569) and Adiyaman University Research Foundation (FEFAAP/2012-0001) for financial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Firat, 23119, Elazig, Turkey

    Zuhal Karagoz Genc & Memet Sekerci

  2. Department of Physiology, Faculty of Medicine, Inonu University, 44280, Malatya, Turkey

    Suat Tekin & Suleyman Sandal

  3. Department of Chemistry, Faculty of Science and Arts, Adiyaman University, 02040, Adiyaman, Turkey

    Murat Genc

Authors
  1. Zuhal Karagoz Genc
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Suat Tekin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Suleyman Sandal
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Memet Sekerci
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Murat Genc
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Zuhal Karagoz Genc or Murat Genc.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Genc, Z.K., Tekin, S., Sandal, S. et al. Synthesis and DFT studies of structural and some spectral parameters of nickel(II) complex with 2-(2-hydroxybenzoyl)-N-(1-adamantyl) hydrazine carbothioamide. Res Chem Intermed 41, 4477–4488 (2015). https://doi.org/10.1007/s11164-014-1545-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1545-5

Keywords

Search

Navigation