Synthesis and Antibacterial Activity of Azomethine Ligand and Their Metal Complexes: A Combined Experimental and Theoretical Study

Khalidah Hamil Manati Al Furaiji(1), Rehab Abdul Mahdi Al Hassani(2), Hanaa Hassan Hussein(3*)

(1) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(2) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(3) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10052, Iraq
(*) Corresponding Author


An asymmetrical Schiff base triazole ligand (4-((3-mercapto-5-(naphthalen-1-ylmethyl)-4H-1,2,4-triazol-4-yl)imino)methyl)methoxy) (L) was used to generate novel micro complexes of Cr(III), VO(IV), and Mn(II) ions. Different spectroscopic techniques, including UV-vis spectroscopy, Fourier transform infrared spectroscopy (FTIR), flame atomic absorption, conductivity tests, CHNS elemental analysis, and magnetic susceptibility, were used to determine the structures of the Schiff base micro complexes. The density functional theory (DFT) calculation was screened to consider selected complexes. The observed data indicated their stability, and the expected chemical formula of vanadium(IV) was square pyramidal geometry in VO(L) complex formula. In contrast, the Cr(III) and Mn(II) complexes have octahedral geometry in the formulas. Frontier molecular orbitals calculations (MO) have also been performed to better understand the nature of orbitals, EHOMO, and ELUMO, allowing us to confirm the experimental finding. Pseudomonas aeruginosa and Bacillus subtilis, two types of potentially dangerous bacteria, were subjected to tests to see whether L and its metal complexes have any antibacterial activities or not. All compounds were also tested for their antifungal activity against two different types of fungi, Penicillium spp. and Aspergillus flavus. There is significant action has been noted in all cases for the complexes.


Schiff base; DFT; transition-metal; antibacterial activity


[1] Mathur, P., and Misra, S., 2020, Metal-carbonyl promoted multicomponent coupling of alkynes for the synthesis of heterocyclic compounds, Adv. Organomet. Chem., 73, 253–304.

[2] Milyushkin, A.L., Birin, K.P., Matyushin, D.D., Semeikin, A.V., Iartsev, S.D., Karnaeva, A.E., Uleanov, A.V., and Buryak, A.K., 2019, Isomeric derivatives of triazoles as new toxic decomposition products of 1,1-dimethylhydrazine. Chemosphere, 217, 95–99.

[3] Brinkmann, M., Schneider, A.L., Bluhm, K., Schiwy, S., Lehmann, G., Deutschmann, B., Müller, A., Tiehm, A., and Hollert, H., 2019, Ecotoxicity of nitrogen, sulfur, or oxygen heterocycles and short-chained alkyl phenols commonly detected in contaminated groundwater, Environ. Toxicol. Chem., 38 (6), 1343–1355.

[4] Dwivedi, A., Singh, S., Kumar, S., and Mittal, P.C., 2020,"Chapter 11 - Organosulfur Phytochemicals against Metabolic and Neurodegenerative Diseases: Benefits and Risks" in Phytochemicals as Lead Compounds for New Drug Discovery, Eds. Egbuna, C., Kumar, S., Ifemeje, J.C., Ezzat, S.M., and Kaliyaperumal, S., Elsevier, Amsterdam, Netherlands, 179–194.

[5] Fayyadh, B.M., Jaafar, W.A., and Sarhan, B.M., 2021, Synthesis, structural study, and biological activity evaluation of VO(II), Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) complexes with new Schiff base ligand derived from pyrazine, Int. J. Drug Delivery Technol., 11 (1), 64–69.

[6] Raouf, H., Beyramabadi, S.A., Allameh, S., and Morsali, A., 2019, Synthesis, experimental and theoretical characterizations of a 1,2,4-triazole Schiff base and its nickel(II) complex, J. Mol. Struct., 1179, 779–786.

[7] Koga, N., and Morokuma, K., 1991, Ab initio molecular orbital studies of catalytic elementary reactions and catalytic cycles of transition-metal complexes, Chem. Rev., 91 (5), 823–842.

[8] Musaev, D.G., and Morokuma, K., 1996,"Advances in chemical physics" in Advances in Chemical Physics, Eds. Prigogine, I., and Rice, S.A., John Wiley & Sons, New York, US, 61–128.

[9] Siegbahn, P.E.M., and Blomberg, M.R.A., 1995, “Oxidative Addition Reactions” in Theoretical Aspects of Homogeneous Catalysis: Applications of Ab Initio Molecular Orbital Theory, Eds. Van Leeuwen, P.W.N.M., Morokuma, K., and Van Lenthe, J.H., Editors, Springer, Dordrecht, Netherlands, 15–63.

[10] Salahub, D.R., Castro, M., Fournier, R., Calaminici, P., Godbout, N., Goursot, A., Jamorski, C., Kobayashi, H., Martínez, A., Pápai, I., Proynov, E., Russo, N., Sirois, S., Ushio, J., and Vela, A., 1994, “Density Functional Description of Metal-Metal and Metal-Ligand Bonds” in Theoretical and Computational Approaches to Interface Phenomena, Eds. Sellers, H.L., and Golab, J.T., Springer US, Boston, MA, 187–218.

[11] Ellouz, M., Sebbar, N.K., Fichtali, I., Ouzidan, Y., Mennane, Z., Charof, R., Mague, J.T., Urrutigoïty, M., and Essassi, E.M., 2018, Synthesis and antibacterial activity of new 1,2,3-triazolylmethyl-2H-1,4-benzothiazin-3(4H)-one derivatives, Chem. Cent. J., 12 (1), 123.

[12] Karpun, Y., Parchenko, V., Fotina, T., Demianenko, D., Fotin, A., Nahornyi, V.V., and Nahorna, N., 2021, The investigation of antimicrobial activity of some S-substituted bis-1,2,4-triazole-3-thiones, Pharmacia, 68 (4), 721–730.

[13] Tratrat, C., Haroun, M., Paparisva, A., Geronikaki, A., Kamoutsis, C., Ćirić, A., Glamočlija, J., Soković, M., Fotakis, C., Zoumpoulakis, P., Bhunia, S.S., and Saxena, A.K., 2018, Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones. Pharmacophore models for antifungal activity, Arabian J. Chem., 11 (4), 573–590.

[14] Othman, A.A., Kihel, M., and Amara, S., 2019, 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents, Arabian J. Chem., 12 (7), 1660–1675.

[15] Matsuzaki, H., Takeda, N., Yasui, M., Okazaki, M., Suzuki, S., and Ueda, M., 2021, Synthesis of multi-substituted 1,2,4-triazoles utilizing the amphiphilic reactivity of hydrazones, Chem. Commun., 57 (91), 12187–12190.

[16] Aswathanarayanappa, C., Bheemappa, E., Bodke, Y.D., Krishnegowda, P.S., Venkata, S.P., and Ningegowda, R., 2013, Synthesis and evaluation of antioxidant properties of novel 1,2,4-triazole-based Schiff base heterocycles, Arch. Pharm., 346 (12), 922–930.

[17] Al-Mansury, S., Balakit, A.A., Alkazazz, F.F., Madlum, K.N., and Ghaleb, R.A., 2019, Synthesis and anti-colon cancer activity of 1,2,4-triazole derivatives with aliphatic S-substituents, Orient. J. Chem., 35 (1), 77–84.

[18] Al-Khazraji, A.M.A., Al Hassani, R.A.M., and Ahmed, A., 2020, Studies on the photostability of polystyrene films with new metals complex of 1, 2, 4-triazole-3-thione derivate, Syst. Rev. Pharm., 11 (5), 525–534.

[19] Zein, N., Shaban, S.M., Shafek, S.H., Baghi, H., Aiad, I., and Omran, M., 2021, Synthesis and characterization of new 1,2,4-triazole anticancer scaffold derivatives: In vitro study, Egypt. J. Chem., 64 (8), 4005–4015.

[20] Deodware, S.A., Barache, U.B., Chanshetti, U.B., Sathe, D.J., Panchsheela Ashok, U., Gaikwad, S.H., and Prasad Kollur, S., 2021, Newly synthesized triazole-based Schiff base ligands and their Co(II) complexes as antimicrobial and anticancer agents: Chemical synthesis, structure and biological investigations, Results Chem., 3, 100162.

[21] Peng, Z., Wang, G., Zeng, Q.H., Li, Y., Wu, Y., Liu, H., Wang, J.J., and Zhao, Y., 2021, Synthesis, antioxidant and anti-tyrosinase activity of 1,2,4-triazole hydrazones as antibrowning agents, Food Chem., 341 (Part 2), 128265.

[22] Bader, A.T., Al-qasii, N.A.R., Shntaif, A.H., El Marouani, M., AL Majidi, M.I.H., Trif, L., and Boulhaoua, M., 2022, Synthesis, structural analysis and thermal behavior of new 1,2,4-triazole derivative and its transition metal complexes, Indones. J. Chem., 22 (1), 223–232.

[23] Al-Alzawi, S.M., Al-Jibouri, M.N., Rasheed, A.M., and Al-Bayati, S.M., 2023, Synthesis, characterization and antimicrobial activity of complexes metal ions Ni(II), Zn(ΙΙ), Pd(II) and Pt(IV) with polydentate 1,2,4-triazole ligand, Indones. J. Chem., 23 (1), 210–218

[24] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., 2016, Gaussian 16, Revision C.01, Gaussian, Inc., Wallingford, CT.

[25] Lu, L., 2015, Can B3LYP be improved by optimization of the proportions of exchange and correlation functionals?, Int. J. Quantum Chem., 115 (8), 502–509.

[26] Al Furaiji, K.H.M., Molino, A., Dutton, J.L., and Wilson, D.J.D., 2020, Theoretical investigation of main-group element hydride insertion into phosphorus-heterocyclic carbenes (PHCs), Aust. J. Chem., 73 (8), 787–793.

[27] Berger, R., 2016, Computational chemistry. Introduction to the theory and applications of molecular and quantum mechanics. Von Errol G. Lewars, Angew. Chem., 116 (38), 5087–5089.

[28] Cheng, G.J., Zhang, X., Chung, L.W., Xu, L., and Wu, Y.D., 2015, Computational organic chemistry: bridging theory and experiment in establishing the mechanisms of chemical reactions, J. Am. Chem. Soc., 137 (5), 1706–1725.

[29] Koch, W., and Holthausen, M.C., 2015, A Chemist's Guide to Density Functional Theory, 2nd Ed., John Wiley & Sons, Weinheim, Germany.

[30] Lee, C., Yang, W., and Parr, R.G., 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B: Condens. Matter Mater. Phys., 37 (2), 785–789.

[31] Al Furaiji, K.H.M., Iversen, K.J., Dutton, J.L., and Wilson, D.J.D., 2018, Theoretical investigation of hydride insertion into N-heterocyclic carbenes containing N, P, C, O and S heteroatoms, Chem. - Asian J., 13 (23), 3745–3752.

[32] Lever, A.B.P., 1984, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam.

[33] Zhang, J., Wang, S., Ba, Y., and Xu, Z., 2019, 1,2,4-Triazole-quinoline/quinolone hybrids as potential anti-bacterial agents, Eur. J. Med. Chem., 174, 1–8.

[34] Patil, B.S., Krishnamurthy, G., Shashikumar, N.D., Lokesh, M.R., and Bhojya Naik, H.S., 2013, Synthesis and antimicrobial activity of some [1,2,4]-triazole derivatives, J. Chem., 2013, 462594.

[35] Barot, K.P., Manna, K.S., and Ghate, M.D., 2017, Design, synthesis and antimicrobial activities of some novel 1,3,4-thiadiazole, 1,2,4-triazole-5-thione and 1,3-thiazolan-4-one derivatives of benzimidazole, J. Saudi Chem. Soc., 21, S35–S43.

[36] Dilmaghani, K.A., Pur, F.N., and Nezhad, M.H., 2015, Synthesis and antibacterial evaluation of new thione substituted 1,2,4-triazole Schiff bases as novel antimicrobial agents, Iran. J. Pharm. Res., 14 (3), 693–699.

[37] Al-Hassani, R.A.M., 2016, Synthesis, structural, antimicrobial activities and theoretical studies of some new trivalent metal complexes with thiocarbamide derivative, Int. J. ChemTech Res., 9 (5), 723–737.

[38] Al-Hassani, R.A.M., and Shaheen, E.S.K., 2013, Synthesis, characterization, theoretical studies and bioactivity of Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes with Mannich base and tryptophane as mixed ligand, Asian J. Biochem. Pharm. Res., 3 (1), 1–27.

[39] Carlin, R.L., and van Duyneveldt, A.J., 1977, Magnetic Properties of Transition Metal Compounds, Springer-Verlag, New York, US.

[40] Greenwood, N.N., and Earnshaw, A., 1998, Chemistry of the Elements, 2nd Ed., Butterworth-Heinemann, Oxford, UK.

[41] Figgis, B.N., and Hitchman, M.A., 1999, Ligand Field Theory and Its Applications, 1st Ed., Wiley-VCH, Weinheim, Germany.

[42] Hussein, H.H., Hussein, F.M., Mohammed, E.Z., and Askar, F.W., 2020, Synthesis, characterization and theoretical study of 2-(2-(thiophen-2-yl)-1H-benzo[d]imidazole-1-yl) acetohydrazide and its complexes, Int. J. Pharm. Res., 12 (2), 1233–1242.


Article Metrics

Abstract views : 120 | views : 51 | views : 23

Copyright (c) 2023 Indonesian Journal of Chemistry

Creative Commons License
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.

Analytics View The Statistics of Indones. J. Chem.