Synthesis, Spectral Identification, Thermal Studies, Antioxidant Properties, and Biological Effects for Some Metal Ion Complexes with New Schiff Base Ligand

Aseel Hikmat Abad Al-Ameer(1*), Naser Shaalan(2)
(1) Department of Chemistry, College of Science, University of Baghdad, Baghdad, Al Jadriya 10070, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Al Jadriya 10070, Iraq
(*) Corresponding Author
Abstract
The tetradentate N2O2 Schiff base ligand, which is produced via the condensation reaction of 2-hydroxynaphthaldehyde with phthalohydrazide, is prepared in this work with a fair yield. The prepared ligand was characterized using a microanalysis technique (C.H.N), UV-vis, FTIR, 1H-,13C-NMR, mass spectrometry, and thermal gravimetric analysis (TGA). New complexes were synthesized by a reaction between ligand (N'1E,N'2Z)-N'1,N'2-bis((1-hydroxynaphthalen-2yl)methylene)phthalohydrazide and metal chloride of Co+2, Ni+2, and Zn+2 ions in absolute ethanol. The present complexes are also characterized by techniques such as C.H.N, UV-vis, FTIR, TGA, molar conductivity, atomic absorption, and magnetic moment measurements. The in vitro antimicrobial activity of the prepared compounds was tested against two Gram-positive bacteria (Staphylococcus aureus and Bacillus) and two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), as well as Candida albicans as a fungal species, by diffusion technique in addition to antioxidant properties. The spectroscopy measurement showed that the ligand coordinated with the metal ion as a tetradentate ligand via oxygen and nitrogen in addition to the chloride ion to form octahedral shapes. All compounds under study had a positive effect against antibacterial, antifungal, and antioxidant activities.
Keywords
References
[1] Nabhan, K.J., Mahdi, A.S., Al-Zaidi, B.H., Ismail, A.H., and Nasif, Z.N., 2022. New tetra-dentate Schiff base ligand N2O2 and its complexes with some of metal ions: Preparation, identification, and studying their enzymatic and biological activities, Baghdad Sci. J., 19 (1), 155.
[2] Afrin Dalia, M., Afsan, F., Saddam Hossain, M., Abdul Mannan, M., Haque, M.M., and Kudrat-E-Zahan, M., 2018, Spectral and thermal characterization of Mn(II), Ni(II) and Zn(II) complexes containing Schiff base ligands towards potential biological application, Asian J. Chem. Sci., 4 (4), 1–11.
[3] El-Sonbati, A.Z., Diab, M.A., Mohamed, G.G., and Morgan, S.M., 2021, Preparation, characterization and biological activity screening on some metal complexes based of Schiff base ligand, Egypt. J. Chem., 64 (8), 4125–4136.
[4] Hussen, N.H., 2023, Synthesis, characterization, molecular docking, ADMET prediction, and anti-inflammatory activity of some Schiff bases derived from salicylaldehyde as a potential cyclooxygenase inhibitor, Baghdad Sci. J., 20 (5), 1662.
[5] Mahdi, S.H., and Abdul Karem, L.K., 2024, Synthesis, characterization, anticancer and antimicrobial studies of metal nanoparticles derived from Schiff base complexes, Inorg. Chem. Commun., 165, 112524.
[6] Fadhel, A.M., Al Hamdani, A.A.S., and Mohamed, S.G., 2024. Synthesis, characterization and antioxidant study of some metal ion complexes with azo 1-(2,4,6-trihydroxy-3-((3-hydroxyphenyl) diazenyl) phenyl) ethan-1-one, Baghdad Sci. J., 21 (12), 3642–3660.
[7] Ishola, K.T., Olaoye, O.J., Oladipo, M.A., Odedokun, O.A., and Aboyeji, O.O., 2023, Synthesis, characterization and antimicrobial properties of mixed-ligand complexes of some metal(II) ions with barbituric acid and 1,10-phenanthroline ligands, Tanzania. J. Sci., 49 (2), 491–502.
[8] Ourari, A., Ketfi, B., and Zerroual, L., 2017, Elaboration of modified poly(NiII-DHS) films as electrodes by the electropolymerization of Ni(II)-[5,5′-dihydroxysalen] onto indium tin oxide surface and study of their electrocatalytic behavior toward aliphatic alcohols, Arabian J. Chem., 10 (7), 914–921.
[9] Sarhan, W.M., Al-Kubaisai, H.M.M., and Al-Hamdani, A.A.S., 2018, Synthesis, spectral, bioactive and theoretical studies of new Schiff base and metal complexes, Res. J. Pharm., Biol. Chem. Sci., 9 (5), 1512–1522.
[10] Ji, Y., Wu, L., Lv, R., Wang, H., Song, S., and Cao, M., 2021, Facile cloud point extraction for the separation and determination of phenolic acids from dandelion, ACS Omega, 6 (20), 13508–13515.
[11] Obaid, S.M.H., Abd-Almonuim, A.E., Al-Naymi, H.A.S., Jarad, A.J., and Saleh, M.M., 2024, Synthesis and characterization of some Metal ions complexes with mixed ligand of azo dye and metformin and evaluation of its effectiveness on the growth of some pathogenic bacteria clinically isolated and study of its toxicity on normal and cancerous hepatocytes, Heliyon, 10 (18), e37849.
[12] Saema, S., Ahmed, T.W., Sharma, P.K., Pathan, I.K., Bhatia, M., and Khan, M., 2023, In vivo and in vitro model for evaluation of anti-microbial activity: A review, Asian J. Pharm. Res., 13 (3), 169–174.
[13] Vlasaku, I., and Tomovska, J., 2024, Determination of antioxidant activity in milk extracts with phosphomolibdate method, SFJD, 5 (11), e4614.
[14] El-Gammal, O.A., El-Bindary, A.A., Sh. Mohamed, F., Rezk, G.N., and El-Bindary, M.A., 2022, Synthesis, characterization, design, molecular docking, anti-COVID-19 activity, DFT calculations of novel Schiff base with some transition metal complexes, J. Mol. Liq., 346, 117850.
[15] Al-Dabbagh, A., Guo, Z., Junk, P., and Wang, J., 2021, Synthesis and characterization of a range of antimony(I/III) N,N′-bis(2,6-diisopropylphenyl)formamidinate complexes, Acta Crystallogr., Sect. C: Struct. Chem., 77 (9), 577–585.
[16] El-Boraey, H.A., Serag El-Din, A.A., and EL-Gammal, O.A., 2021, Design, spectroscopic characterization, thermal, 3D molecular modeling, XRD and in vitro antioxidant and antimicrobial screening of novel N2O2 tetradentate Schiff’s base metal complexes, Egypt. J. Chem., 64 (9), 5153–5166.
[17] Mohamed, E.A., Negm, N.A., Youssef, A.O., and Sayed, G.H., 2024, Preparation, characterization, and spectroscopic properties of a novel iron(III), copper (II), and nickel (II) complexes with Schiff base ligand derived from salicylaldehyde and p–phenylene diamine on polyvinyl chloride photodegradation, Egypt. J. Chem., 67 (1), 225–238.
[18] Hassan, S.S., Hassan, N.M., Baqer, S.R., and Saleh, A.M., 2021, Biological evaluation and theoretical study of bi-dentate ligand for amoxicillin derivative with some metal ions, Baghdad Sci. J., 18 (4), 1269–1278.
[19] Shaalan, N., 2022, Preparation, spectroscopy, biological activities and thermodynamic studies of new complexes of some metal ions with 2-[5-(2-hydroxy-phenyl)-1,3,4-thiadiazol-2-ylimino]-methyl-naphthalen-1-ol, Baghdad Sci. J., 19 (4), 829–837.
[20] Isyaku, S., Aliyu, H.N., Abubakar, T., and Bello, J., 2020, Synthesis, characterization and antimicrobial studies of iron(II) and cobalt(II) complexes of a Schiff base derived from 2-acetylthiophene with 4-phenylthiosemicarbazide, J. Chem. Soc. Niger., 45(1), 29–37.
[21] Hussein, K.A., Mahdi, S., and Shaalan, N., 2023, Synthesis, spectroscopy of new lanthanide complexes with Schiff base derived from (4-antipyrinecarboxaldehyde with ethylene di-amine) and study the bioactivity, Baghdad Sci. J., 20 (2), 469–482.
[22] Majeed, N.M., Abd. Al-Sahab, S., and Al Shemary, R.K., 2021, Eco-friendly and efficient composition, diagnosis, theoretical, kinetic studies, antibacterial and anticancer activities of mixed some metal complexes of tridentate Schiff base ligand, Int. J. Pharm. Res., 13 (1), 3358–3369.
[23] Hussain, I., Ullah, A., Khan, A.U., Khan, W.U., Ullah, R., Naser, A.A.S., and Mahmood, H.M., 2019, Synthesis, characterization and biological activities of hydrazone Schiff base and its novel metals complexes, Sains Malays., 48 (7), 1439–1446.
[24] Abd Dleam, E., and Kareem, S.H., 2021. Mesoporous silica nanoparticles as a system for ciprofloxacin drug delivery; kinetic of adsorption and releasing, Baghdad Sci. J., 18 (2), 357–357.
[25] Fadhil, Z., Zageer, D.S., Faris, A.H., Al-Mashhadani, M.H., Ahmed, A., Hashim, H., and Yousif, E., 2022, Extracted lignin from oil palm empty fruit bunch as natural eco-friendly poly(vinyl chloride) photo-stabilizer, Mater. Sci. Energy Technol., 5, 15–21.
[26] Tang, K., Wang, X.X., Zhao, J.J., Ren, N., and Zhang, J.J., 2024. The investigation of crystal structure, thermodynamic properties, and fluorescence properties of three new rare earth coordination compounds, Arabian J. Chem., 17 (1), 105462.
[27] Saleh, R.H., Rashid, W.M., Dalaf, A.H., Al-Badrany, K.A., and Mohammed, O.A., 2020, Synthesis of some new thiazolidinone compounds derived from Schiff bases compounds and evaluation of their laser and biological efficacy, Ann. Trop. Med. Public Health, 23 (7), 1012–1031.
[28] Kargar, H., Aghaei-Meybodi, F., Behjatmanesh-Ardakani, R., Elahifard, M.R., Torabi, V., Fallah-Mehrjardi, M., Tahir, M.N., Ashfaq, M., and Munawar, K.S., 2021, Synthesis, crystal structure, theoretical calculation, spectroscopic and antibacterial activity studies of copper(II) complexes bearing bidentate Schiff base ligands derived from 4-aminoantipyrine: Influence of substitutions on antibacterial activity, J. Mol. Struct., 1230, 129908.
[29] Himalian, R., and Singh, M.P., 2022, A comparative account on antioxidant activities, total phenolic and flavonoid contents of Punica granatum, Carica papaya, Foeniculum vulgare, Trigonella foenum-graecum, and Urtica dioica: An in vitro evaluation, Res. J. Pharm. Technol., 15 (3), 1175–1183.
[30] Bouacha, M., Besnaci, S., and Boudiar, I., 2023, An overview of the most used methods to determine the in vitro antibacterial activity of honey, Acta Microbiol. Bulg., 39 (1), 23–30.
[31] Rahman, A.K.M.L., Sarker, A., Bashir, M.N., and Hossain, M.L., 2023, Molybdenum(VI) complexes of N,N′-bis isatin diamine Schiff base: Synthesis and characterization, Bangladesh J. Sci. Ind. Res., 58 (4), 201–208.
[32] Sami, S., and Shaalan, N., 2024, Synthesis, structure, and biological activity studies of new metal ion complexes based on 3-[(3-hydroxynaphthalene-2-yl-ethylidene)-hydrazono]-1,3-dihydro-indol-2-one, Indones. J. Chem., 24 (2), 370–378.

Article Metrics



Copyright (c) 2025 Indonesian Journal of Chemistry

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.