Synthesis, Characterization and Biological Activity of Mixed Ligand (Imine of Benzidine and 1,10-Phenanthroline) Complexes with Fe(II), Co(II), Ni(II) and Cu(II) Ions

: pp. 15–24
Department of Chemistry, College of Science, University of Kerbala
Department of Chemistry, College of Science, University of Kerbala
Department of Chemistry, College of Science, University of Kerbala
Department of Chemistry, College of Science, University of Kerbala
Department of Biology, College of Science, University of Kerbala

In this paper, binuclear metal complexes of the metal ions Fe(II), Co(II), Ni(II) and Cu(II) were synthesized by the reaction of the primary ligand (imine of benzidine) (H2L) and the secondary ligand (1,10-phenanthroline) (L`) with these metal ions in a molar ratio of 1:2:2, respectively. The complexes were characterized using CHN elemental analysis, FT-IR, UV-Vis, magnetic susceptibility, molar conductivity, 1H NMR, and TGA-DTA thermogravimetric analysis. According to the results obtained from the elemental analysis and spectral measurements where complexes of Fe(II), Co(II) and Ni(II) have octahedral geometry, while the complex with Cu(II) has a square planar geometry. All the prepared complexes are wholly stable and can keep for months without any significant change. The antibacterial activities of the prepared compounds were evaluated with regard to two bacteria species, gram-negative Proteus and Kelbsiella, by using diffusion agar plates. The inhibition zone diameter around the holes indicated the sensitivity of the bacteria to these compounds, where the Klebsiella bacteria were revealed to be more highly sensitive to these compounds than Proteus bacteria. All synthesized complexes showed more significant effects against Kelbsiella and Protea than the antibiotic (Amikacin).

  1. Yousif, E.; Majeed, A.; Al-Sammarrae, K.; Salih N.; Salimon J.; Abdullah B. Metal Complexes of Schiff base: Preparation, Characterization and Antibacterial Activity. Arab. J. Chem. 2017, 10, 1639-1644.
  2. Ejidike, I.; Ajibade, P. Ruthenium(III) Complexes of Heterocyclic Tridentate (ONN) Schiff Base: Synthesis, Characterization and its Biological Properties as an Antiradical and Antiproliferative Agent. Int. J. Mol. Sci. 2016, 17, 60.
  3. Murtaza, S.; Akhtar, M.; Kanwal, F.; Abbas, A.; Ashiq, S.; Shamim S. Synthesis and Biological Evaluation of Schiff Bases of 4-Aminophenazone as an Anti-inflammatory, Analgesic and Antipyretic Agent. J. Saudi Chem. Soc. 2017, 21, 359-372.
  4. Divya, K.; Pinto, G.; Pinto, A. Application of Metal Complexes of Schiff Bases as an Antimicrobial Drug: A Review of Recent Works. Int. J. Curr. Pharm. Res. 2017, 9, 27-30.
  5. Anacona, J.; Mago, K.; Camus, J. Antibacterial Activity of Transition Metal Complexes with a Tridentate NNO Amoxicillin Derived Schiff Base. Synthesis and Characterization. Appl. Organomet. Chem. 2018, 32, 1.
  6. Barnabas, M.; Parambadath, S.; Nagappan, S.; Ha, C. Sulfamerazine Schiff-Base Complex Intercalated Layered Double Hydroxide: Synthesis, Characterization, and Antimicrobial Activity. Heliyon. 2019, 5, e01521.
  7. Sunday Nworie, F. Bis(Salicylidene) Ethylenediamine(salen) and bis(Salicylidene) Ethylenediamine-Metal Complexes: from Structure to Biological Activity. J. Anal. Pharm. Res. 2016, 3, 1.
  8. Akhter, S.; Zaman, H.; Mir, S. Dar, A.M. Synthesis of Schiff Base Metal Complexes: A Concise Review. Eur. Chem. Bull. 2017, 6, 475-483.
  9. Rao, N.; Mishra, D.; Maurya, R. Synthesis and Characterisation of Some Novel CIS-Dioxo-Molybdenum(VI) Complexes of Schiff Bases Derived from Salicylaldehyde. Synth. React. Inorg. Met. Chem. 1995, 25, 437-449.
  10. Felthouse, T.; Hendrickson, D. Magnetic Exchange Interactions in Binuclear Transition-Metal Complexes. 17. Benzidine and p-Phenylenediamine, Extended Aromatic Diamine Bridging Ligands in Binuclear Copper(II) 2,2',2''-triaminotriethylamine and Vanadyl Bis(hexafluoroacetylacetonate) Complexes. Inorg. Chem. 1978, 17, 2636-2648.
  11. El-Tabl, A. Synthesis and Physico-Chemical Studies on Cobalt(II), Nickel(II) and Copper(II) Complexes of Benzidine Diacetyloxime Transit. Met. Chem. 2002, 27, 166-170.
  12.  Zhao, P.; Zhai, S.; Dong, J.: Gao, L.; Liu X.; Wang L.; Kong J.; Li L. Synthesis, Structure, DNA Interaction, and SOD Activity of Three Nickel(II) Complexes Containing L-Phenylalanine Schiff Base and 1,10-Phenanthroline. Bioinorg. Chem. Appl. 2018, 2018, 8478152.
  13. Patel, R. N.; Singh, N. G.; Gundla, V.L.N. Synthesis, Structure and Properties of Ternary Copper(II) Complexes of ONO Donor Schiff Base, Imidazole, 2,2′-Bipyridine and 1,10-Phenanthroline. Polyhedron 2006, 25, 3312-3318.
  14. Kosolapov, D.; Kuschak, P.; Vainshtein, M.; Vatsourina, A.V.; Weiβner, A.; Kästner, M.; Müller, R.A. Microbial Processes of Heavy Metal Removal from Carbon-Deficient Effluents in Constructed Wetlands. Eng. Life Sci. 2004, 4, 403-411.
  15. Selvamohan, T.; Sandhya, V. Studies on Bactericidal Activity of Different Soaps Against Bacterial Strains J. Microbiol. Biotechnol. Res. 2012, 2, 646-650.
  16. Bauer, A.W.; Kirby, W.M.M.; Sherris, J.C.; Turck, M. Antibiotic Susceptibility Testing by a Standardized Single Disk Method: Am. J. Clin. Pathol. 1966, 45, 493-496.
  17. More, G.; Raut, D.; Aruna, K.; Bootwala, S. Synthesis, Spectroscopic Characterization and Antimicrobial Activity Evaluation of New Tridentate Schiff Bases and their Co(II) Complexes. J. Saudi Chem. Soc. 2017, 21, 954-964.
  18. Singh, D.K.; Singh, N.; Singh, R. Transethmoidal Meningocele: an Unusual Complication of Intracranial Neoplasm. Int. J. Inorg. Chem. 2013, 2013, 1.
  19. Krishnaveni, G.; Mubarak, M.S; Kiruthika, M.; Elayaperumal, R. Synthesis, Spectral Characterization, Electrochemical Behaviour, In vitro Antimicrobial and DPPH Radical Scavenging Activities of Iron (II), Cobalt (II) Complexes with Imidazolyl Terpyridine. Der Chem. Sin. [Online] 2017, 8. (accessed Oct 06, 2021).
  20. Larsen, C.; Wenger, O. Photoredox Catalysis with Metal Complexes Made from Earth-Abundant Elements. Chem A Eur J., 2018, 24, 2039-2058.
  21. San Tan, S.; Yanagisawa, S.; Inagaki, K.; Kassim, M.B.; Morikawa, Y. Experimental and Computational Studies on Ruthenium(ii) bis-Diimine Complexes of N,N′-chelate Ligands: the Origin of Changes in Absorption Spectra Upon Oxidation and Reduction. Phys. Chem. Chem. Phys. 2019, 21, 7973.
  22. Goodgame, D.M.L.; Goodgame, M.; Cotton, F.A. Electronic Spectra of Some Tetrahedral Nickel(II) Complexes. J. Am. Chem. Soc., 1961, 83, 4161-4167.
  23. Lever, A. Inorganic Electronic Spectroscopy, 2nd ed.; Elsevier Pub. Co: Amsterdam, New York, 1968.
  24. Mihsen, H.H.; Shareef N.D. Synthesis, Characterization of Mixed-Ligand Complexes Containing 2,2-Bipyridine and 3-Aminopropyltriethoxysilane. J. Phys. Conf. Ser. 2018, 1032, 1.
  25. Venanzi, L.M. Tetrahedral Complexes of Nickel (II) and the Factors Determining their Formation. J. Inorg. Nucl. Chem. 1958, 8(C), 137-142.
  26. Knittl, E.T.; Abou-Hussein, A.A.; Linert, W. Syntheses, Characterization, and Biological Activity of Novel Mono- and Binuclear Transition Metal Complexes with a Hydrazone Schiff Base Derived from a Coumarin Derivative and Oxalyldihydrazine. Monatshefte für Chemie-Chemical Mon. 2018, 149, 431-443.
  27. Mihsen, H.H.; Abass, S.K.; Abass, A.K.; Hussain, K.A.; Abbas, Z.F. Template Synthesis of Sn(II), Sn(IV) and Co(II) Complexes via 3-Aminopropyltriethoxysilane and Salicylaldehyde and Evaluate their Antibacterial Sensitivity. Asian J. Chem. 2018, 30, 2277-2280.
  28. Czakis-Sulikowska, D.; Malinowska, A.; Radwañska-Doczekalska, J. Synthesis, Properties and Thermal Decomposition of Bipyridine-Oxalato Complexes with Mn(II), Co(II), Ni(II) and Cu(II). Pol. J. Chem. 2000, 74, 607-614.
  29. Pearson, R.G. Hard and Soft Acids and Bases. J. Am. Chem. Soc. 1963, 85, 3533-3539.
  30. Sundaram, S.; Kanniappan, G.V.; Kannappan, P. Enzymatic and Non Enzymatic Antioxidant Activity of Tabernaemontana divaricate R.Br. against DEN and Fe-NTA Induced Renal Damage in Wistar Albino Rats. J. Appl. Pharm. Sci. 2015, 5, 33-37.