Synthesis, Characterization and Antioxidant of Azo Ligand, Cr(III), Mn(II), and Mo(VI) Complexes

https://doi.org/10.22146/ijc.114337

Shrouq Masad Khdair Al-Dulaimi(1), Abbas Ali Salih Al-Hamdani(2*)

(1) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract


This paper presents a novel azo dye prepared by reacting a diazonium salt derived from 4-methylbenzene-1,2-diamine with 3,5-dimethylphenol. This dye was used to synthesize a new series of mononuclear compounds with the formulas [Cr(L)Cl(H2O)], [Mn(L)(H2O)2], and [MoO2L]. Various measurements were performed on the prepared materials to determine the proposed formulations, including infrared, ultraviolet-visible, and mass spectrometry measurements, as well as thermogravimetric and elemental analysis. The conductivity, magnetic susceptibility, metal content, and chlorine content of the compounds were also evaluated. The complexes prepared from the dye were used to assess their ability to inhibit free radicals by measuring their antioxidant capacity using DPPH as the free radical and gallic acid as the standard, and determining the IC50 value. The ability of the compounds to inhibit free radicals varied according to their IC50 values and their comparison with ascorbic acid. The Mo complex gave the highest ability to inhibit free radicals compared to the rest of the compounds with the order as follows: Gallic acid > [MoO2L] > LH2 > [Cr(L)(H2O)Cl] > [Mn(L)(H2O)2] These suggest that the synthesized metal–azo dye complexes, particularly the Mo complex, have promising potential as antioxidant agents and may be useful for future applications in pharmaceutical field.


Keywords


antioxidant; azo dyes; metal complexes; 4-methylbenzene-1; 2-diamine; thermal analysis



References

[1] Bukia, Y., Utiashvili, M., Tsiskarishvili, M., Jalalishvili, S., Gogolashvili, A., Tatrishvili, T., and Petriashvili, G., 2023, Synthesis of some azo dyesbased on 2,3,3-trimethyl-3H-idolenine, Chem. Technol., 17 (3), 549–556.

[2] Al-Naemi, A.AA., Al-Hamdani, A.A.S., Ahmed, S.D., Rabbee, M.F., Park, N., and Al Zoubi, W., 2025, Synthesis, characterization, antioxidant and bioactivity assessment, and thermodynamic analysis of metal ion complexes using a novel azo dye, Chin. J. Anal. Chem., 53 (10), 100586.

[3] Gaber, M., Fathalla, S.K., and El-Ghamry, H.A., 2019, 2,4-Dihydroxy-5-[(5-mercapto-1H-1,2,4-triazole-3-yl)diazenyl]benzaldehyde acetato, chloro and nitrato Cu(II) complexes: Synthesis, structural characterization, DNA binding and anticancer and antimicrobial activity, Appl. Organomet. Chem., 33 (4), e4707.

[4] Saad, F.A., El‐Ghamry, H.A., and Kassem, M.A., 2019, Synthesis, structural characterization and DNA binding affinity of new bioactive nano‐sized transition metal complexes with sulfathiazole azo dye for therapeutic applications, Appl. Organomet. Chem., 33 (7), e4965.

[5] Shamran Mohammed, H., Munahi, M.G., Al-nayili, A., Swadi Zghair, F., Zizi, Z., Abdulhadi Al-Asadi, D., and Alhamzawi, G., 2025, Synthesis, characterization and fingerprint identification enhancement by deep learning for azo dye derived from amino pyridine and caffeine and its palladium complex, Bull. Chem. Soc. Ethiop., 39 (11), 2173–2184.

[6] Shamran Mohammed, H., Deepak Tripathi, V., Aldin Darghouth, A., and Mothhar, T., 2019 Synthesis, characterization, DFT calculation and antimicrobial activity of Co(II) and Cu(II) complexes with azo dye, J. Phys.: Conf. Ser., 1294 (5), 052051.

[7] Jirjees, V.Y., Suleman, V.T., Salih Al-Hamdani, A.A., and Ahmed, S.D., 2019, Preparation, spectroscopic characterization, and theoretical studies of transition metal complexes with 1-[(2-(1H-indol-3-yl)ethylimino)methyl]naphthalene-2-ol ligand, Asian J. Chem., 31 (11), 2430–2438.

[8] Nakbi, H., Dallel, W., Hammami, S., and Mighri, Z., 2020, Phytochemical profile and antioxidant properties of leaves extracts from Posidonia oceanica (L.) Delile and their allelopathic potential on terrestrial plant species, Bull. Chem. Soc. Ethiop., 34 (3), 437–447.

[9] Torrado G, J.F., Aguilar-Muñoz, G.A., Sandoval-Hernandez, A.G., Rodríguez B, O., and Castellanos, N.J., 2026, Synthesis, spectroscopic characterization and cytotoxicity studies of new potential anticancer chemotherapeutics, cis-dioxidomolybdenum(VI) compounds with substituted polypyridyl ligands, J. Mol. Struct., 1352, 144562.

[10] Sabar, S.S., Alajrawy, O., Elbohy, S.A.H., and Sharaby, C.M., 2022, New molybdenum(VI) and vanadium(IV) complexes with 3-aminopyridine and dithiooxamide ligands spectroscopic characterization, DFT calculations, and in vitro cytotoxic activity, Mater. Today: Proc., 65, 2537–2550.

[11] Al-Hamdani, A.A.S., and Abdulridha, M.Q., 2023. Synthesis, characterization of new metal complexes of Co(II), Cu(II), Cd(II) and Ru(III) from azo ligand 5-((2-(1H-indol-2-yl)ethyl) diazinyl)-2-aminophenol, thermal and antioxidant studies, Baghdad Sci. J., 20 (Suppl. 5), 1964–1975.

[12] Abdulrazzaq, A.G., and Al-Hamdani, A.A.S., 2023, Ni2+, Pt4+, Pd2+, and Mn2+ metal ions complexes with azo derived from quinolin-2-ol and 3-amino-N-(5-methylisoxazol-3-yl) benzenesulfonamide: Synthesis, characterization, thermal study, and antioxidant activity, Baghdad Sci. J., 20 (6), 2207–2223.

[13] Gaber, M., Khedr, A.M., and Mansour, M.A., 2018, Nano-synthesis, characterization, modeling and molecular docking analysis of Mn(II), Co(II), Cr(III) and Cu(II) complexes with azo pyrazolone ligand as new favorable antimicrobial and antitumor agents, Appl. Organomet. Chem., 32 (12), 4606.

[14] Al-Rubaye, N.T.A., Ahmed, S.D., Al-Hamdani, A.A.S., Alhamoud, L., and Al Zoubi, W., 2026, Synthesis, characterization, and evaluation of the antioxidant and anticancer activities of metal ion complexes with a novel 7-(3-hydroxyphenylazo)-quinolin-8-ol ligand, Chin. J. Anal. Chem., 54 (1), 100617.

[15] Silverstein, R.M., Webster, X.F., and Kiemle, D.J., 2005, Spectrometric Identification of Organic Compounds, John Wiley & Son, Hoboken, New Jersey, US.

[16] Al-Daffay, R.K.H., and Al-Hamdani, A.A.S., 2023, Synthesis, characterization, and thermal analysis of a new acidic azo ligand's metal complexes, Baghdad Sci. J., 20 (1), 121–133.

[17] Abd El-Lateef, H.M., Khalaf, M.M., Amer, A.A., Kandeel, M., Abdelhamid, A.A., and Abdou, A., 2023, Synthesis, characterization, antimicrobial, density functional theory, and molecular docking studies of novel Mn(II), Fe(III), and Cr(III) complexes incorporating 4-(2-hydroxyphenyl azo)-1-naphthol (Az), ACS Omega, 8 (29), 25877–25891.

[18] Hussein, N.H., and Mahdi, R.T., 2019, Synthesis, spectral characterization, thermal analysis, antimicrobial and antitumor properties of new azo ligand with some of its transition metal complexes, Int. J. Pharm. Res., 11 (1), 618–637.

[19] El-Ghamry, H.A., Alkurbi, A.A., Alhasani, M.A., Takroni, K.M., and Khedr, A.M., 2023, Copper based azo dye catalysts for phenoxazinone synthase mimicking efficiency: Structure characterization and bioactivity evaluation, Arabian J. Chem., 16 (12), 104916.

[20] Nagasundaram, N., Govindhan, C., Sumitha, S., Sedhu, N., Raguvaran, K., Santhosh, S., and Lalitha, A., 2022, Synthesis, characterization and biological evaluation of novel azo fused 2,3-dihydro-1H-perimidine derivatives: In vitro antibacterial, antibiofilm, anti-quorum sensing, DFT, in silico ADME and molecular docking studies, J. Mol. Struct., 12448, 131437.

[21] Yousef, T.A., Abu El-Reash, G.M., Abu AL-Zahab, M., and Safaan, M.A.A., 2019, Physicochemical investigations, biological studies of the Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and UO2(VI) complexes of picolinic acid hydrazide derivative: A combined experimental and computational approach, J. Mol. Struct., 1197, 564–575.

[22] Alaghaz, A.N.M.A., Ammar, Y.A., Bayoumi, H.A., and Aldhlmani, S.A., 2014, Synthesis, spectral characterization, thermal analysis, molecular modeling and antimicrobial activity of new potentially N2O2 azo-dye Schiff base complexes, J. Mol. Struct., 1074, 359–375.

[23] Sönmez, M., Sogukomerogullari, H.G., Öztemel, F., and Berber, İ., 2014, Synthesis and biological evaluation of a novel ONS tridentate Schiff base bearing pyrimidine ring and some metal complexes, Med. Chem. Res., 23 (7), 3451–3457.

[24] Vinodkumar, V., and Keshavayya, J., 2019, Synthesis, structural investigations and in vitro biological evaluation of N,N-dimethyl aniline derivatives based azo dyes as potential pharmacological agents, J. Mol. Struct., 1186, 404–412.

[25] Mandour, H.S., Abouel-Enein, S.A., Morsi, R.M.M., and Khorshed, L.A., 2021, Azo ligand as new corrosion inhibitor for copper metal: Spectral, thermal studies and electrical conductivity of its novel transition metal complexes, J. Mol. Struct., 1225, 129159.

[26] Ahmadi, R.A., and Amani, S., 2012, Synthesis, spectroscopy, thermal analysis, magnetic properties and biological activity studies of Cu(II) and Co(II) complexes with Schiff base dye ligands, Molecules, 17 (6), 6434–6448.

[27] Mahmoodi, N.O., Ahmadi, A., Yazdani Nyaki, H., Taherpour Nahzomi, H., and Panahi Kokhdan, E., 2022, Efficient synthesis of new azo-sulfonamide derivatives and investigation of their molecular docking and cytotoxicity results, Arabian J. Chem.,15 (12), 104383.

[28] 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.

[29] Manhee, T.Q., and Alabdali, A.J., 2024, Synthesis, characterization and anticancer activity of Ni(II), Cu(II), Pd(II) and Au(III) complexes derived from novel Mannich base, Vietnam J. Chem., 62 (2), 201–210.

[30] Abd, S.S., Alkam, H.H., and Al-Shemary, R.K.R., 2023, Composition, depiction, antibacterial, antioxidant, and cytotoxicity activities studies of anew nano-sized binuclear metal(II) Schiff base complexes, AIP Conf. Proc., 2414 (1), 050011.



DOI: https://doi.org/10.22146/ijc.114337

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