Skip to main content
Log in

Supramolecular structure, spectroscopic, thermal studies and antimicrobial activities of Schiff base complexes

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

Abstract

Metal(II) complexes of 4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (HL) were prepared, and their compositions and physicochemical properties were characterized on the basis of elemental analysis, with1HNMR, UV–Vis, IR, mass spectroscopy and thermogravimetric analysis. All results confirm that the novel complexes have a 1:1 (M:HL) stoichiometric formulae [M(HL)Cl2] (M = Cu(II)(1), Cd(II)(5)), [Cu(L)(O2NO)(OH2)2](2), [Cu(HL)(OSO3)(OH2)3]2H2O(3), [Co(HL)Cl2(OH2)2]3H2O(4), and the ligand behaves as a neutral/monobasic bidentate/tridentate forming a five/six-membered chelating ring towards the metal ions, bonding through azomethine nitrogen, exocyclic carbonyl oxygen, and/or deprotonated phenolic oxygen atoms. The XRD studies show that both the ligand and Cu(II) complex (1) show polycrystalline with monoclinic crystal structure. The molar conductivities show that all the complexes are non-electrolytes. On the basis of electronic spectral data and magnetic susceptibility measurements, a suitable geometry has been proposed. The trend in g values (g ll > g  > 2.0023) suggest that the unpaired electron on copper has a \(d_{{x^{2} - y^{2} }}\) character, and the complex (1) has a square planar, while complexes (2) and (3) have a tetragonal distorted octahedral geometry. The molecular and electronic structures of the ligand (HL) and its complexes (15) have been discussed. Molecular docking was used to predict the binding between HL ligand and the receptors of the crystal structure of Escherichia coli (E. coli) (3t88) and the crystal structure of Staphylococcus aureus (S. aureus) (3q8u). The activation thermodynamic parameters, such as activation energy (E a), enthalpy (ΔH), entropy (ΔS), and Gibbs free energy change of the decomposition (ΔG) are calculated using Coats–Redfern and Horowitz–Metzger methods. The ligand and its metal complexes (15) showed antimicrobial activity against bacterial species such as Gram positive bacteria (Bacillus cereus and S. aureus), Gram negative bacteria (E. coli and Klebsiella pneumoniae) and fungi (Aspergillus niger and Alternaria alternata); the complexes exhibited higher activity than the ligand.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15

Similar content being viewed by others

References

  1. M.S. Refat, M.Y. El-Sayed, J. Mol. Struct. 1038, 62–72 (2013)

    Article  CAS  Google Scholar 

  2. A.A. Nejo, G.A. Kolawole, A.O. Nejo, J. Coord. Chem. 63, 4398–4410 (2010)

    Article  CAS  Google Scholar 

  3. C. Andraud, I.V. Kityk, H. Kutawara, G. Lemercier, K. Stromberger, M. Alexandre, W. Gruhn, K.S. Pak, Mater. Lett. 57, 1489–1495 (2003)

    Article  CAS  Google Scholar 

  4. M. Sonmez, A. Levent, M. Sekerci, Russ. J. Coord. Chem. 30, 655–659 (2004)

    Article  Google Scholar 

  5. S.P. Fricker, Dalton Trans. 43, 4903–4917 (2007)

    Article  Google Scholar 

  6. R.R. Crichton, D.T. Dexter, R.J. Ward, Coord. Chem. Rev. 252, 1189–1199 (2008)

    Article  CAS  Google Scholar 

  7. R. Cini, G. Tamasi, S. Defazio, M.B. Hursthouse, J. Inorg. Biochem. 101, 1140–1152 (2007)

    Article  CAS  Google Scholar 

  8. A.M. Asiri, K.O. Badahdah, S.A. Khan, A.G. Al-Sehemi, M.S. Al-Amoudi, A.A. Bukhari, Org. Chem. Insights 3, 1–8 (2010)

    Article  CAS  Google Scholar 

  9. A. Blagus, D. Cinčić, T. Friščić, B. Kaitner, V.S. Macedonian, J. Chem. Eng. 29, 117–138 (2010)

    CAS  Google Scholar 

  10. H. Unver, M. Kabak, D.M. Zengin, T.N. Durlu, J. Chem. Crystallogr. 31, 203–209 (2001)

    Article  CAS  Google Scholar 

  11. M. Yıldız, H. Unver, D. Erdener, N. Ocak, A. Erdonmez, T.N. Durlu, Cryst. Res. Technol. 41, 600–606 (2006)

    Article  Google Scholar 

  12. Z. Rozwadowski, W. Schlif, B. Kamienski, Magn. Reson. Chem. 43, 573–577 (2005)

    Article  CAS  Google Scholar 

  13. J. Matijevic-Sosa, M. Vinkovic, D. Vikic-Topic, Croat. Chem. Acta 79, 489–495 (2006)

    CAS  Google Scholar 

  14. S.H. Alarcon, A.C. Olivieri, D. Sanz, R.M. Claramunt, J. Elguero, J. Mol. Struct. 705, 1–9 (2004)

    Article  CAS  Google Scholar 

  15. P.V. Rao, C.P. Rao, E.K. Wegelius, K. Rissanen, J. Chem. Crystallogr. 33, 139–147 (2003)

    Article  CAS  Google Scholar 

  16. A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, G.G. Mohamed, ShM Morgan, M.I. Abou-Dobara, S.G. Nozha, J. Mol. Liq. 215, 423–442 (2016)

    Article  CAS  Google Scholar 

  17. A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, M.I. Abou-Dobara, H.A. Seyam, Spectrochim. Acta A 104, 213–221 (2013)

    Article  CAS  Google Scholar 

  18. A.A. El-Bindary, A.F. Shoair, A.Z. El-Sonbati, M.A. Diab, E.E. Abdo, J. Mol. Liq. 212, 576–584 (2015)

    Article  CAS  Google Scholar 

  19. M.A. Diab, A.Z. El-Sonbati, A.A. El-Bindary, G.G. Mohamed, ShM Morgan, Res. Chem. Intermed. 41, 9029–9066 (2015)

    Article  CAS  Google Scholar 

  20. A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, A.M. Eldesoky, ShM Morgan, Spectrochim. Acta A 135, 774–791 (2015)

    Article  CAS  Google Scholar 

  21. M.J. Waring, J. Mol. Biol. 13, 269–282 (1965)

    Article  CAS  Google Scholar 

  22. M.F. Reichmann, C.A. Rice, C.A. Thomos, P. Doty, J. Am. Chem. Soc. 76, 3047–3053 (1954)

    Article  CAS  Google Scholar 

  23. A. Wolfe, G.H. Shimer, T. Meehan, Biochem. 26, 6392–6396 (1987)

    Article  CAS  Google Scholar 

  24. P.W. Selwood, Magnetic Chemistry (Interscience Publishers Inc, New York, 1956)

    Google Scholar 

  25. R. Shirley “The CRYSFIRE System for Automatic Powder Indexing”: User’s Manual, the Lattice Press, Guildford, Surrey GU2 7NL, England (2000)

  26. J. Laugier, B. Bochu, LMGP-suite suite of programs for the interpretation of X-ray experiments. ENSP/Laboratoire des Materiaux et du Genie Physique, BP46, 38042, Saint Martin d’Heres, France (2000)

  27. N.A. El-Ghamaz, M.A. Diab, A.A. El-Bindary, A.Z. El-Sonbati, H.A. Seyam, J. Mater. Sci. Semicond. Proc. 27, 521–531 (2014)

    Article  CAS  Google Scholar 

  28. N.A. El-Ghamaz, A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, G.G. Mohamed, ShM Morgan, Spectrochim. Acta A. 147, 200–211 (2015)

    Article  CAS  Google Scholar 

  29. T.A. Halgren, J. Computat. Chem. 17, 490–519 (1998)

    Article  Google Scholar 

  30. G.M. Morris, D.S. Goodsell, J. Comput. Chem. 19, 1639–1662 (1998)

    Article  CAS  Google Scholar 

  31. W.J. Geary, Coord. Chem. Rev. 7, 81–122 (1971)

    Article  CAS  Google Scholar 

  32. L. Antonov, W.M.F. Fabian, D. Nedeltcheva, F.S. Kamounah, J. Chem. Soc. Perkin Trans. 22, 1173–1179 (2000)

    Article  Google Scholar 

  33. M.A. Diab, A.Z. El-Sonbati, A.A. El-Bindary, ShM Morgan, M.K. Abd El-Kader, J. Mol. Liq. 218, 571–585 (2016)

    Article  CAS  Google Scholar 

  34. K. Sakata, M. Hashinoto, T. Hamada, S. Massuno, Polyhedron 15, 967–972 (1966)

    Article  Google Scholar 

  35. D.P. Singh, K. Kumar, C. Sharma, Euro. J. Med. Chem. 44, 3299–3304 (2008)

    Article  Google Scholar 

  36. M.A. Diab, A.Z. El-Sonbati, R.H. Mohamed, Spectrochim. Acta A 77, 795–801 (2010)

    Article  CAS  Google Scholar 

  37. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 3rd edn. (Wiley Interscience, New York, 1978)

    Google Scholar 

  38. A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, G.G. Mohamed, ShM Morgan, Inorg. Chim. Acta 430, 96–107 (2015)

    Article  CAS  Google Scholar 

  39. M.M. Ghoneim, A.Z. El-Sonbati, A.A. El-Bindary, M.A. Diab, L.S. Serag, Spectrochim. Acta A 140, 111–131 (2015)

    Article  CAS  Google Scholar 

  40. A.A. El-Bindary, A.Z. El-Sonbati, M.A. Diab, ShM Morgan, J. Mol. Liq. 201, 36–42 (2015)

    Article  CAS  Google Scholar 

  41. E.M. El-Menyawy, N.A. El-Ghamaz, H.H. Nawar, J. Mol. Struct. 1036, 144–150 (2013)

    Article  CAS  Google Scholar 

  42. N.A. El-Ghamaz, A.A. El-Bindary, A.Z. El-Sonbati, N.M. Beshry, J. Mol. Liq. 211, 628–639 (2015)

    Article  CAS  Google Scholar 

  43. N.A. El-Ghamaz, M.A. Diab, A.A. El-Bindary, A.Z. El-Sonbati, H.A. Seyam, J. Mater. Sci. Semicond. Process. 27, 521–531 (2014)

    Article  CAS  Google Scholar 

  44. A.B.P. Lever, Inorganic Electronic Spectroscopy, 1st edn. (Elsevier, Amsterdam, 1968), p. 249

    Google Scholar 

  45. D. Kivelson, R. Neiman, J. Chem. Phys. 35, 149–155 (1961)

    Article  CAS  Google Scholar 

  46. N.R.S. Kumar, M. Nethiji, K.C. Patil, Polyhedron 10, 365–371 (1991)

    Article  CAS  Google Scholar 

  47. N.A. El-Ghamaz, A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, ShM Morgan, Mater. Res. Bull. 65, 293–301 (2015)

    Article  CAS  Google Scholar 

  48. N. Raman, C. Thangaraja, Trans. Met. Chem. 30, 317–322 (2005)

    Article  CAS  Google Scholar 

  49. A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd edn. (Elsevier, Amsterdam, 1984)

    Google Scholar 

  50. V.V. Pavlishchuk, S.P. Kolotilov, A.W. Addison, R.J. Butcher, E. Sinn, J. Dalton Trans. 335–341 (2000)

  51. A.Z. El-Sonbati, A.A. El-Bindary, G.G. Mohamed, ShM Morgan, W.M.I. Hassan, A.K. Elkholy, J. Mol. Liq. 218, 16–34 (2016)

    Article  CAS  Google Scholar 

  52. J.W. Searl, R.C. Smith, S.J. Wyard, Proc. Phys. Soc. 78, 1174–1176 (1961)

    Article  CAS  Google Scholar 

  53. P. Kamalakamman, D. Venkappayya, Russ. J. Coord. Chem. 28, 423 (2002)

    Article  Google Scholar 

  54. S.N. Shitte, A.S.R. Murty, G.L. Tembe, Indian J. Chem. 32A, 318 (1993)

    Google Scholar 

  55. T. Ahamad, V. Kumar, S. Parveen, N. Nishat, J. Coord. Chem. 61, 47–56 (2008)

    Google Scholar 

  56. N.S. Bhave, A.S. Aswar, Asian J. Chem. 4, 65–72 (1992)

    CAS  Google Scholar 

  57. B.N. Figgis, Introduction to Ligand Fields (Interscience, New York, 1966), p. 295

    Google Scholar 

  58. B.J. Hathaway, Struct. Bond. 14, 49–67 (1973)

    Article  CAS  Google Scholar 

  59. S. Chandra, D. Jain, A.K. Sharma, Spectrochim. Acta A 71, 1712–1719 (2009)

    Article  Google Scholar 

  60. A.W. Coats, J.P. Redfern, Nature 20, 68–79 (1964)

    Article  Google Scholar 

  61. H.W. Horowitz, G. Metzger, Anal. Chem. 35, 1464–1468 (1963)

    Article  CAS  Google Scholar 

  62. M.I. Abou-Dobara, A.Z. El-Sonbati, ShM Morgan, World J. Microbiol. Biotechnol. 29, 119–126 (2013)

    Article  CAS  Google Scholar 

  63. A.A. El-Bindary, G.G. Mohamed, A.Z. El-Sonbati, M.A. Diab, W.M.I. Hassan, ShM Morgan, A.K. Elkholy, J. Mol. Liq. 218, 138–149 (2016)

    Article  CAS  Google Scholar 

  64. A.Z. El-Sonbati, G.G. Mohamed, A.A. El-Bindary, W.M.I. Hassan, M.A. Diab, ShM Morgan, A.K. Elkholy, J. Mol. Liq. 212, 487–502 (2015)

    Article  CAS  Google Scholar 

  65. J.P. Costes, F. Dahan, J.P. Laurent, M. Drillon, Inorg. Chem. Acta 294, 8–12 (1999)

    Article  CAS  Google Scholar 

  66. D.K. Jangir, S.K. Dey, S. Kundu, R. Mehrotra, J. Photochem. Photobiol. B 114, 38–43 (2012)

    Article  CAS  Google Scholar 

  67. K. Benner, H. Ihmels, S. Kölsch, P.M. Pithan, Org. Biomol. Chem. 12, 1725–1734 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank Miss N.F. Omar, Botany Department, Faculty of Science, Damietta University, Egypt for her help during testing antimicrobial activity.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Z. El-Sonbati.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

El-Sonbati, A.Z., El-Bindary, A.A., Diab, M.A. et al. Supramolecular structure, spectroscopic, thermal studies and antimicrobial activities of Schiff base complexes. Res Chem Intermed 43, 577–629 (2017). https://doi.org/10.1007/s11164-016-2641-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2641-5

Keywords

Navigation