SYNTHESIZED, CHARACTERIZATION, AND INVESTIGATED ANTIOXIDANT PROPERTIES OF NOVEL HYDRAZON COMPLEXES OF MANGANES(II), COBALT(II), NICKEL(II), COPPER(II), AND ZINC(II)
Keywords:
Transition metals, Antioxidant activity, Hydrazones, Complexes
Abstract
A series of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of hydrazones derived from dibenzoyl methane and aroylhydrazines namely benzoyl hydrazine(DBMBH), 2-furoyl hydrazine (DBMFH) and picolinoyl hydrazine(DBMPH), were synthesized and characterized by elemental and thermal analysis, molar conductance, magnetic properties, IR, 1H-NMR, 13C-NMR, and UV-Vis spectra measurements. Spectroscopic analysis showed that the ligands acted as tridentate ONO donors to the central metal ion. Physio-chemical investigations indicate that complexes with Mn(II), Co(II), Ni (II), Cu (II), and Zn (II) have octahedral, tetrahedral, and square-planar geometries. The measurement of the molar conductance of these compounds in DMSO and in methanol revealed that they are non-electrolytic in nature. The ligand and its metal complexes were tested with DPPH to determine whether or not they have anti-oxidant action. Based on the data that was gathered, it was clear that the ligand has stronger antioxidant properties than its metal complexes
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References
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Hosny, N. M. (2011). Synthesis and Characterization of Transition Metal Complexes Derived from (E)-N-(1-(Pyridine-2-yl) ethylidiene) benzohydrazide (PEBH). Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41(7), 736-742.
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Singh, Y. P., & Patel, S. K. (2021). Molecular structures, spectral, electrochemical, DFT and antioxidant activities of copper (II) complexes with NNO donor Schiff base ligand. Journal of Molecular Structure, 1228, 129457.
Zhang, L., Zhang, J. P., & Zhu, D. Y. (2005). Synthesis, characterization and antibacterial activities of (N‐Oxide Pyridinyl‐2‐Aldehyde)‐3, 5‐Dibenzyloxybenzoylhydrazone and its complexes. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 35(4), 295-298.
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Devi, J., Batra, N., & Malhotra, R. (2012). Ligational behavior of Schiff bases towards transition metal ion and metalation effect on their antibacterial activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 397-405.
Mohapatra, R. K., Dash, M., Mishra, U. K., Mahapatra, A., & Dash, D. C. (2014). Synthesis, spectral characterization, and fungicidal activity of transition metal complexes with benzimidazolyl-2-hydrazones of glyoxal, diacetyl, and Benzil. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44(5), 642-648.
Kanchanadevi, S., Fronczek, F. R., David, C. I., Nandhakumar, R., & Mahalingam, V. (2021). Investigation of DNA/BSA binding and cytotoxic properties of new Co (II), Ni (II) and Cu (II) hydrazone complexes. Inorganica Chimica Acta, 526, 120536.
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Singh, V. P., Singh, S., Singh, D. P., Singh, P., Tiwari, K., Mishra, M., & Butcher, R. J. (2013). Synthesis, spectral and single crystal X-ray diffraction studies on Co (II), Ni (II), Cu (II) and Zn (II) complexes with o-amino acetophenone benzoyl hydrazone. Polyhedron, 56, 71-81.
Sharma, A. K., & Chandra, S. (2013). Synthesis, structural and fungicidal studies of hydrazone based coordination compounds. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 103, 96-100.
Özdemir, Ü. Ö., Akkaya, N., & Özbek, N. (2013). New nickel (II), palladium (II), platinum (II) complexes with aromatic methanesulfonylhydrazone based ligands. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation. Inorganica Chimica Acta, 400, 13-19.
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Singh, P. K., & Kumar, D. N. (2006). Spectral studies on cobalt (II), nickel (II) and copper (II) complexes of naphthaldehyde substituted aroylhydrazones. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 64(4), 853-858..
El-Motaleb, A., Ramadan, M., & Issa, R. M. (2005). Synthesis, characterization and ascorbic acid oxidase mimetic catalytic activity of copper (II) picolyl hydrazone complexes. Transition metal chemistry, 30, 471-480.
Santiago, P. H., Santiago, M. B., Martins, C. H., & Gatto, C. C. (2020). Copper (II) and zinc (II) complexes with Hydrazone: Synthesis, crystal structure, Hirshfeld surface and antibacterial activity. Inorganica Chimica Acta, 508, 119632.
Al-Hazmi, G. A., & El-Asmy, A. A. (2009). Synthesis, spectroscopy and thermal analysis of copper (II) hydrazone complexes. Journal of Coordination Chemistry, 62(2), 337-345.
Elsayed, S. A., Butler, I. S., Claude, B. J., & Mostafa, S. I. (2015). Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes. Transition Metal Chemistry, 40, 179-187..
Saleh, R. A., Mohammad, H. A., & Saber, S. N. A. (2020). New Mixed Ligand Cobalt (II), Nickel (II) and Copper (II) Complexes of 2, 2'-Bipyridine-3, 3'-Dicarboxylic acid (bpdc) with 2-Mercapto-5-Phenyl-1, 3, 4-Oxadiazole (phozSH) and Their Antioxidant activity. Oriental Journal of Chemistry, 36(5), 834.
Zhang, L., & Tang, N. (2007). Synthesis and Characterization of Benzoyl Vanillin Hydrazone and its Complexes with Biological Activities. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 37(3), 185-188.
Abouzayed, F. I., Emam, S. M., & Abouel-Enein, S. A. (2020). Synthesis, characterization and biological activity of nano-sized Co (II), Ni (II), Cu (II), Pd (II) and Ru (III) complexes of tetradentate hydrazone ligand. Journal of Molecular Structure, 1216, 128314.
Aly, S. A., & Fathalla, S. K. (2020). Preparation, characterization of some transition metal complexes of hydrazone derivatives and their antibacterial and antioxidant activities. Arabian Journal of Chemistry, 13(2), 3735-3750..
Al-Fulaij, O. A., Jeragh, B., El-Sayed, A. E. M., El-Defrawy, M. M., & El-Asmy, A. A. (2015). Chelation, spectroscopic characterization, biological activity and crystal structure of 2, 3-butanedione isonicotinylhydrazone: Determination of Zr4+ after flotation separation. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 136, 1834-1841.
Hosseini-Monfared, H., Bikas, R., Sanchiz, J., Lis, T., Siczek, M., Tucek, J., ... & Mayer, P. (2013). Syntheses, structures and magnetic properties of azido-and phenoxo-bridged complexes of manganese containing tridentate aroylhydrazone based ligands. Polyhedron, 61, 45-55.
Alfares, A.A., Alnuaimy, L.A. and Al-Daher, A.G.M., (2022). Synthesis and Characterization of Mn (II), Co (II), Ni (II), Cu (II) and Zn (II) complexes with 2-Carboxy benzaldehyde Aroylhydrazones. Egyptian Journal of Chemistry, 65(1), pp.1-2.
Al-Ne’aimi, M. M. (2012). Synthesis and characterization of bis-acylhydrazone derivatives as tetradentate ligands and their dinuclear metal (II) complexes. Chem. Engineering, 56, 83-90.
El-Tabl, A. S., El-Saied, F. A., Plass, W., & Al-Hakimi, A. N. (2008). Synthesis, spectroscopic characterization and biological activity of the metal complexes of the Schiff base derived from phenylaminoacetohydrazide and dibenzoylmethane. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71(1), 90-99.
Al-Hakimi, A. N., El-Tabl, A. S., & Shakdofa, M. M. (2009). Coordination and biological behaviour of 2-(p-toluidino)-N'-(3-oxo-1, 3-diphenylpropylidene) acetohydrazide and its metal complexes. Journal of Chemical Research, 2009(12), 770-774.
Choudhary, A., Sharma, R., Nagar, M., Mohsin, M., & Meena, H. S. (2011). Synthesis, characterization and antioxidant activity of some transition metal complexes with terpenoid derivatives. Journal of the Chilean Chemical Society, 56(4), 911-917.
Jeragh, B., & El-Asmy, A. A. (2014). Coordination of Fe (III), Co (II), Ni (II), Cu (II), Zn (II), Cd (II), Hg (II), Pd (II) and Pt (II) with 2, 5-hexanedione bis (thiosemicarbazone), HBTS: crystal structure of cis-[Pd (HBTS)] Cl2 and 1-(2, 5-dimethyl-1H-pyrrol-yl)-thiourea. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 130, 546-552.
Bekheit, M. M., El-Shobaky, A. R., & Allah, M. T. G. (2017). Synthesis and characterization studies of new five member ring metal chelates derived from benzion phenoxyacetyl hydrazone (H2BPAH). Arabian Journal of Chemistry, 10, S1973-S1979.
Sathyadevi, P., Krishnamoorthy, P., Jayanthi, E., Butorac, R. R., Cowley, A. H., & Dharmaraj, N. (2012). Studies on the effect of metal ions of hydrazone complexes on interaction with nucleic acids, bovine serum albumin and antioxidant properties. Inorganica Chimica Acta, 384, 83-96.
Hosny, N. M., & Shallaby, A. H. M. (2007). Spectroscopic characterization of some metal complexes derived from 4-acetylpyridine nicotinoylhydrazone. Transition Metal Chemistry, 32(8), 1085-1090.
Mitu, L., Ilis, M., Raman, N., Imran, M., & Ravichandran, S. (2012). Transition metal complexes of isonicotinoyl–hydrazone-4-diphenylaminobenzaldehyde: synthesis, characterization and antimicrobial studies. E-Journal of Chemistry, 9(1), 365-372.
Patil, S. A., Unki, S. N., Kulkarni, A. D., Naik, V. H., & Badami, P. S. (2011). Synthesis, characterization, in vitro antimicrobial and DNA cleavage studies of Co (II), Ni (II) and Cu (II) complexes with ONOO donor coumarin Schiff bases. Journal of Molecular Structure, 985(2-3), 330-338.
Hosny, N. M. (2011). Synthesis and Characterization of Transition Metal Complexes Derived from (E)-N-(1-(Pyridine-2-yl) ethylidiene) benzohydrazide (PEBH). Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 41(7), 736-742.
El-Tabl, A. S., El-Saied, F. A., & Al-Hakimi, A. N. (2008). Spectroscopic characterization and biological activity of metal complexes with an ONO trifunctionalized hydrazone ligand. Journal of Coordination Chemistry, 61(15), 2380-2401.
Singh, Y. P., & Patel, S. K. (2021). Molecular structures, spectral, electrochemical, DFT and antioxidant activities of copper (II) complexes with NNO donor Schiff base ligand. Journal of Molecular Structure, 1228, 129457.
Zhang, L., Zhang, J. P., & Zhu, D. Y. (2005). Synthesis, characterization and antibacterial activities of (N‐Oxide Pyridinyl‐2‐Aldehyde)‐3, 5‐Dibenzyloxybenzoylhydrazone and its complexes. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 35(4), 295-298.
Sathyadevi, P., Krishnamoorthy, P., Alagesan, M., Thanigaimani, K., Muthiah, P. T., & Dharmaraj, N. (2012). Synthesis, crystal structure, electrochemistry and studies on protein binding, antioxidant and biocidal activities of Ni (II) and Co (II) hydrazone complexes. Polyhedron, 31(1), 294-306.
Banerjee, S., Ray, A., Sen, S., Mitra, S., Hughes, D. L., Butcher, R. J., ... & Turner, D. R. (2008). Pseudohalide-induced structural variations in hydrazone-based metal complexes: Syntheses, electrochemical studies and structural aspects. Inorganica Chimica Acta, 361(9-10), 2692-2700.
Devi, J., Batra, N., & Malhotra, R. (2012). Ligational behavior of Schiff bases towards transition metal ion and metalation effect on their antibacterial activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 397-405.
Mohapatra, R. K., Dash, M., Mishra, U. K., Mahapatra, A., & Dash, D. C. (2014). Synthesis, spectral characterization, and fungicidal activity of transition metal complexes with benzimidazolyl-2-hydrazones of glyoxal, diacetyl, and Benzil. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44(5), 642-648.
Kanchanadevi, S., Fronczek, F. R., David, C. I., Nandhakumar, R., & Mahalingam, V. (2021). Investigation of DNA/BSA binding and cytotoxic properties of new Co (II), Ni (II) and Cu (II) hydrazone complexes. Inorganica Chimica Acta, 526, 120536.
Mangalam, N. A., Kurup, M. P., Suresh, E., Kaya, S., & Serdaroğlu, G. (2021). Diversities in the chelation of aroylhydrazones towards cobalt (II) salts: synthesis, spectral characterization, crystal structure and some theoretical studies. Journal of Molecular Structure, 1232, 129978..
Singh, V. P., Singh, S., Singh, D. P., Singh, P., Tiwari, K., Mishra, M., & Butcher, R. J. (2013). Synthesis, spectral and single crystal X-ray diffraction studies on Co (II), Ni (II), Cu (II) and Zn (II) complexes with o-amino acetophenone benzoyl hydrazone. Polyhedron, 56, 71-81.
Sharma, A. K., & Chandra, S. (2013). Synthesis, structural and fungicidal studies of hydrazone based coordination compounds. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 103, 96-100.
Özdemir, Ü. Ö., Akkaya, N., & Özbek, N. (2013). New nickel (II), palladium (II), platinum (II) complexes with aromatic methanesulfonylhydrazone based ligands. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation. Inorganica Chimica Acta, 400, 13-19.
Rakha, T. H., El-Gammal, O. A., Metwally, H. M., & El-Reash, G. A. (2014). Synthesis, characterization, DFT and biological studies of (Z)-N′-(2-oxoindolin-3-ylidene) picolinohydrazide and its Co (II), Ni (II) and Cu (II) complexes. Journal of Molecular Structure, 1062, 96-109.
Singh, P. K., & Kumar, D. N. (2006). Spectral studies on cobalt (II), nickel (II) and copper (II) complexes of naphthaldehyde substituted aroylhydrazones. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 64(4), 853-858..
El-Motaleb, A., Ramadan, M., & Issa, R. M. (2005). Synthesis, characterization and ascorbic acid oxidase mimetic catalytic activity of copper (II) picolyl hydrazone complexes. Transition metal chemistry, 30, 471-480.
Santiago, P. H., Santiago, M. B., Martins, C. H., & Gatto, C. C. (2020). Copper (II) and zinc (II) complexes with Hydrazone: Synthesis, crystal structure, Hirshfeld surface and antibacterial activity. Inorganica Chimica Acta, 508, 119632.
Al-Hazmi, G. A., & El-Asmy, A. A. (2009). Synthesis, spectroscopy and thermal analysis of copper (II) hydrazone complexes. Journal of Coordination Chemistry, 62(2), 337-345.
Elsayed, S. A., Butler, I. S., Claude, B. J., & Mostafa, S. I. (2015). Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes. Transition Metal Chemistry, 40, 179-187..
Saleh, R. A., Mohammad, H. A., & Saber, S. N. A. (2020). New Mixed Ligand Cobalt (II), Nickel (II) and Copper (II) Complexes of 2, 2'-Bipyridine-3, 3'-Dicarboxylic acid (bpdc) with 2-Mercapto-5-Phenyl-1, 3, 4-Oxadiazole (phozSH) and Their Antioxidant activity. Oriental Journal of Chemistry, 36(5), 834.
Zhang, L., & Tang, N. (2007). Synthesis and Characterization of Benzoyl Vanillin Hydrazone and its Complexes with Biological Activities. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 37(3), 185-188.
Published
2023-09-20
How to Cite
SULEMAN, V. T., & AL-DAHER, A. G. M. (2023). SYNTHESIZED, CHARACTERIZATION, AND INVESTIGATED ANTIOXIDANT PROPERTIES OF NOVEL HYDRAZON COMPLEXES OF MANGANES(II), COBALT(II), NICKEL(II), COPPER(II), AND ZINC(II). Journal of Duhok University, 26(2), 90-105. https://doi.org/10.26682/sjuod.2023.26.2.9
Section
Pure and Engineering Sciences
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