Synthesis, structural and spectroscopic properties of Co(II), Ni(II) and Cu(II) complexes with 2-((2-chlorobenzylidene)amino) acetohydrazide hydrate and their Antimicrobial and antioxidant activities

Main Article Content

Fathi Mohammed Al-Azab
Yasmin Mosa’d Jamil
Amani Ahmed Al-Gaadbi

Abstract

The current study was purposed to prepare Co(II), Ni(II) and Cu(II) complexes with the ligands derived from 2-chlorobenzaldehyde, glycine and hydrazine hydrate. The obtained compounds were characterized by different physicochemical studies such as elemental analysis, atomic absorption, molar ratio analysis, electronic absorption (UV-Vis spectroscopy), magnetic properties, FTIR spectroscopy, 1H–NMR, 13C-NMR, conductance measurements and XRD. Antimicrobial and antioxidant activities were also calculated. The antibacterial activity was evaluated by the diffusion method against two Gram-positive and two Gram-negative bacteria, while antifungal activity was assessed against two fungal strains by using the agar method. The ligand with Schiff base and hydrazide groups and its complexes showed better biological activity. The results showed that the most metal complexes have much higher antibacterial and antifungal activity compared to the parent ligand. The antioxidant activity of 3.7453 mg of the ligand exhibited excellent activity as the activity of 1 mg of ascorbic acid which is used as a standard antioxidant.


 

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Al-Azab, F. M., Jamil, Y. M., & Al-Gaadbi, A. A. (2023). Synthesis, structural and spectroscopic properties of Co(II), Ni(II) and Cu(II) complexes with 2-((2-chlorobenzylidene)amino) acetohydrazide hydrate and their Antimicrobial and antioxidant activities. Eclética Química, 48(2), 66–82. https://doi.org/10.26850/1678-4618eqj.v48.2.2023.p66-82
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Original articles

References

Abed, A. H.; Khodair Z. T.; Al-Saadi, T. M.; Al-Dhahir, T. A. Study the evaluation of Williamson–Hall (W-H) strain distribution in silver nanoparticles prepared by sol-gel method. AIP Conf. Proc. 2019, 2123 (1), 020019. https://doi.org/10.1063/1.5116946

Al Zoubi, W. Biological Activities of Schiff Bases and Their Complexes: A Review of Recent Works. Int. J. Org. Chem. 2013, 3 (3A), 73–95. https://doi.org/10.4236/ijoc.2013.33A008

Al-Garawi, Z. S. M.; Tomi, I. H. R.; Al-Daraji, A. H. R. Synthesis and characterization of new amino acid-Schiff bases and studies their effects on the activity of ACP, PAP and NPA enzymes (In Vitro). J. Chem. 2012, 9 (2), 962–969. https://doi.org/10.1155/2012/218675

Ali, M. A.; Majumder, S. M. M.-u.-H.; Butcher, R. J.; Jasinski, J. P.; Jasinski, J. M. The preparation and characterization of bis-chelated nickel(II) complexes of the 6-methylpyridine-2-carboxaldehyde Schiff bases of S-alkyldithiocarbazates and the X-ray crystal structure of the bis {S-methyl-β-N-(6-methylpyrid-2-yl)- methylenedithiocarbazato}nickel(II) complex. Polyhedron 1997, 16 (16), 2749–2754. https://doi.org/10.1016/S0277-5387(97)00036-3

Al-Jiboury, M. M.; Al-Nama, K. S. Preparation, Characterization and Biological Activities of some Unsymmetrical Schiff bases derived from m-phenyelenediamine and their metal complexes. Raf. J. Sci. 2019, 28 (2), 23–36. https://doi.org/10.33899/rjs.2019.159965

Al-Maydama, H. M.; Abduljabbar, A. A.; Al-Maqtari, M. A.; Naji, K. M. Study of temperature and irradiation influence on the physicochemical properties of aspirin. J. Mol. Struct. 2018, 1157, 364–373. https://doi.org/10.1016/j.molstruc.2017.12.062

Alomari, A. A. Synthesis, characterization and electrochemical studies of Cu(II), Fe(II), Fe(III) and Ni(II) complexes of Someo-phenylenediamine Schiff base. Master’s Thesis, University of Malaya Kuala Lumpur, Kuala Lumpur, 2010.

Al-Salami, B. K.; Gata, R. A.; Asker, K. A. Synthesis Spectral, Thermal Stability and Bacterial Activity of Schiff Bases Derived from Selective Amino Acid and Their Complexes. Adv. Appl. Sci. Res. 2017, 8 (3), 4–12.

Al-Salami, B. K.; Ul-Saheb, R. G. A.; Asker, K. A. Synthesis spectral, thermal stability and antibacterial activity of schiff bases derived from alanine and threonine and their complexes. J. Chem. Pharm. Res. 2015, 7 (8), 792–803.

Ashraf, M. A.; Mahmood, K.; Wajid, A. Synthesis, Characterization and Biological Activity of Schiff Bases. IPCBEE. 2011, 10, 1–7.

Demirbaş, N. Demirbaş, A.; Sancak, K. Synthesis and characterization of some 3-alkyl-4-amino-5-cyanomethyl-4H-1,2,4-triazoles. Turk J. Chem. 2002, 26, 801–806.

Dzulkifli, N. N.; Farina, Y.; Baba, I.; Ibrahim, N. Synthesis, structural, antibacterial and spectral studies of Co(II) complexes with salicylaldehyde and p-chlorobenzaldehyde 4-phenylthiosemicarbazone. Malaysian J. Anal. Sci. 2012, 16 (2), 103–109.

Ejelonu, B. C.; Oyeneyin, O. E.; Olagboye, S. A.; Akele, O. E. Synthesis, characterization and antimicrobial properties of transition metal complexes of aniline and sulphadiazine Schiff bases as mixed ligands. J. Chem. Pharm. Res. 2018, 10 (5), 67–73.

Emriye, A. Y. Synthesis and characterization of Schiff base 1-Amino-4-methylpiperazine derivatives. CBU J. of Sci. 2016, 12 (3), 375–392.

Gao, H. Synthesis, Characterisation and transition metal ion complexation studies of “pocket-like” imine and amide derivatives. Doctoral Dissertation, National University of Ireland Maynooth, Maynooth, 2013.

Ghara, A.; Si, A.; Majumder, M.; Bagchi, A.; Raha, A.; Mukherjee, P.; Pal, M.; Saha, R.; Bassu, S. A detailed study of Transition Metal Complexes of a Schiff base with its Physico- chemical properties by using an electrochemical method. AJPP. 2017, 3 (3), 86–94.

Hossain, S.; Banu, L. A.; E-Zahan, K.; Haque, M. Synthesis, characterization and biological activity studies of mixed ligand complexes with Schiff base and 2,2-bipyridine. Int. J. Appl. Sci. Res. Rev. 2019, 6 (1–2), 1–7.

Jamil, Y. M. S.; Al-Azab, F. M.; Al-Selwi, N. A.; Alorini, T.; Al-Hakimi, A. N. Preparation, physicochemical characterization, molecular docking and biological activity of a novel Schiff-base and organophosphorus Schiff base with some transition metal(II) ions. Main Group Chemistry 2022, Pre-press, 1–26. https://doi.org/10.3233/MGC-220101

Kapadnis, K. H.; Jadhav, S. P.; Patil, A. P.; Hiray, A. P. Four synthesis methods of Schiff base ligands and preparation of their metal complex with Ir and antimicrobial investigation. WJPPS. 2016, 5 (2), 1055–1063.

Mahmood, T. H.; Hassan, E. A.; Mubark, L. A. Preparation and characterization of Co(II), Ni(II) and Cu(II) ions binuclear complexes with macrocyclic Schiff base derived from acidhydrazide and α-hydroxy ketone. JUAPS. 2013, 7 (2).

Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Acid hydrazides, potent reagents for synthesis of oxygen-, nitrogen-, and/or sulfur-containing heterocyclic rings. Chem. Rev. 2014, 114 (5), 2942–2977. https://doi.org/10.1021/cr300122t

Malakyan, M.; Babayan, N.; Grigoryan, R.; Sarkisyan, N.; Tonoyan, V.; Tadevosya, D.; Matosyan, V.; Aroutiounian, R.; Arakelyan, A. Synthesis, characterization and toxicity studies of pyridinecarboxaldehydes and L-tryptophan derived Schiff bases and corresponding copper (II) complexes. F1000 Research. 2016, 5, 1921. https://doi.org/10.12688/f1000research.9226.1

Mathew, G.; Susselan, M. S.; Krishnan, R. Synthesis and characterisation of cobalt (II) complexes of chromen-2-one-3-carboxy hydrazide and 2-(chromen-2-onyl)-5-(aryl)1,3,4-oxadiazoe derivatives. Indian J. Chem. 2006, 45A, 2040–2044.

Mishra, A. P.; Sharma, N.; Jain, R. K. Microwave Synthesis, Spectral, Thermal and antimicrobial studies of some Ni(II) and Cu(II) Schiff base complexes. Avances en Química 2012, 7 (1), 77–85.

Mohamed, E. A.; Mohamed, B.; Mustapha, H. Synthesis and characterization of N-salicylidèneglycinate (KHL) and caffeine complexes with Cd (II), Cu (II), Ni (II), Zn (II). IJCPS. 2014, 3 (5), 22–34.

Mohamed, G. G.; Omar; M. M.; Hindy, A. M. Metal Complexes of Schiff Bases: Preparation, Characterization and Biological Activity. Turk J. Chem. 2006, 30, 361–382.

Naji, K. M.; Thamer, F. H.; Numan, A. A.; Dauqan, E. M.; Alshaibi, Y. M.; D’souza, M. R. Ferric-bipyridine assay: A novel spectrophotometric method for measurement of antioxidant capacity. Heliyon. 2020, 6 (1), E03162. https://doi.org/10.1016/j.heliyon.2020.e03162

Neelofar, N. A.; Khan, A.; Amir, S.; Khan, N. A.; Bilal, M. Synthesis of Schiff bases derived from 2-hydroxy-1-naphth- aldehyde and their tin(II) complexes for antimicrobial and antioxidant activities. Bull. Chem. Soc. Ethiop. 2017, 31 (3), 445–456. https://doi.org/10.4314/bcse.v31i3.8

Oğuzhan, B.; Campolat, E.; Şahal, H.; Kaya, M. The synthesis, characterization of a novel Schiff base ligand and investigation of its transition metal complexes. Adyu. J. Sci. 2017, 7 (1), 47–59.

Omer, D. A.; Al-Daher, A. G. M. New tridentate hydrazone metal complexes derived from 2-hydroxy-4-methoxyacetophenone and some acid hydrazides: synthesis, characterization and antibacterial activity evaluation. Raf. J. Sci. 2019, 28 (2), 100–111. https://doi.org/10.33899/rjs.2019.159969

Patel, K. S.; Patel, J. C.; Dholariya, H. R.; Patel, V. K.; Patel, K. D. Synthesis of Cu(II), Ni(II), Co(II), and Mn(II) Complexes with Ciprofloxacin and Their Evaluation of Antimicrobial, Antioxidant and Anti-Tubercular Activity. Open J. Met. 2012, 2 (3), 49–59. https://doi.org/10.4236/ojmetal.2012.23008

Refat, M. S.; Al-Maydama, H. M. A.; Al-Azab, F. M.; Amin, R. R.; Jamil, Y. M. S. Synthesis, thermal and spectroscopic behaviors of metal – drug complexes: La (III), Ce(III), Sm(III) and Y(III) amoxicillin trihydrate antibiotic drug complexes. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014a, 128, 427–446. https://doi.org/10.1016/j.saa.2014.02.160

Refat, M. S.; Al-Azab, F. M.; Al-Maydama, H. M. A.; Amin, R. R.; Jamil, Y. M. S. Synthesis and in vitro microbial evaluation of La(III), Ce(III), Sm(III) and Y(III) metal complexes of vitamin B6 drug. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014b, 127, 196–215. https://doi.org/10.1016/j.saa.2014.02.043

Refat, M. S.; Al-Azab, F. M.; Al-Maydama, H. M. A.; Amin, R. R.; Jamil, Y. M. S.; Kobeasy, M. I. Synthesis, spectroscopic and antimicrobial studies of La(III), Ce(III), Sm(III) and Y(III) metformin HCl chelates. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 142, 392–404. https://doi.org/10.1016/j.saa.2015.01.096

Reiss, A.; Cioteră, N.; Dobrițescu, A.; Rotaru, M.; Carabete, A. C.; Parisi, F.; Gănescu, A.; Dăbuleanu, I.; Spînu, C. I.; Rotaru, P. Bioactive Co(II), Ni(II), and Cu(II) complexes containing a tridentate sulfathiazole-based (ONN) Schiff base. Molecules. 2021, 26 (10), 3062. https://doi.org/10.3390/molecules26103062

Safoura, F. Novel Synthesis of Schiff bases Bearing Glucosamine Moiety. Res. J. Chem. Sci. 2014, 4 (2), 25–28.

Sakhare, D. T.; Chondhekar, T. K.; Shankarwar, S. G.; Shankarwar, A. G. Synthesis, characterization of some transition metal complexes of bidentate Schiff base and their antifungal and antimicrobial studies. Adv. Appl. Sci. Res. 2015, 6 (6), 10–16.

Salawu, O. W.; Wuana, R. A.; Ashimom, J. T. Synthesis, characterization and corrosion inhibition of Co (II), Ni (II), Cu (II), and Zn (II) complexes derived from nicotinic acid hydrazide. In 39th CSN Annual International Conference. Port Harcourt: Academic Journals; 2018, pp 2–6.

Sarwar, A.; Shamsuddin, M. B.; Lingtang, H. Synthesis, characterization and luminescence studies of metal-diimine complexes. Mod. Chem. Appl. 2018, 6 (3), 1000262. https://doi.org/10.4172/2329-6798.1000262

Savalia, R. V.; Patel, A. P.; Trivedi, P. T.; Gohel, H. R.; Khetani, D. B. Rapid and economic synthesis of Schiff base of salicylaldehyde by microwave irradiation. Res. J. Chem. Sci. 2013, 3 (10), 97–99.

Sharma, P. K.; Sen, A. K.; Dubey, S. N. Synthetic, spectral and thermal studies of cobalt(ІІ), nickel(ІІ), zinc(ІІ) and cadmium(ІІ) complexes with amino acid Schiff bases. Indian J. Chem. 1994, 33 (A), 1031–1033.

Shneine, J. K.; Qassem, D. Z.; Mahmoud, S. S. Synthesis, characterization, and antibacterial activity of some amino acid derivatives. Int. J. Chemtech Res. 2017, 10 (3), 604–612.

Tulu, M. M.; Yimer, A. M. Catalytic Studies on Schiff Base Complexes of Co (II) and Ni (II) using benzoylation of phenol. Mod. Chem. Appl. 2018, 6 (3), 1000260. https://doi.org/10.4172/2329-6798.1000260

Yousef, E.; Radwan, L.; Othman, M. A. Synthesis of Co (ІІ) and Cu (ІI) complexes with NO and N2O2 ligands derived from salicylaldehyde. Chem. Mater. Res. 2016, 8 (7), 82–93.