Synthesis and Characterization of a Novel Azo-Dye Schiff Base and Its Metal Ion Complexes Based on 1,2,4-Triazole Derivatives

https://doi.org/10.22146/ijc.83509

Nada Ahmed Rasheed Al-qasii(1), Ali Taleb Bader(2*), Zaied Mosaa(3)

(1) Department of Chemistry, College of Science, University of Baghdad, Baghdad 11001, Iraq
(2) Department of Chemistry, College of Sciences for Woman, University of Babylon, Hilla 51001, Iraq
(3) Department of Chemistry, College of Sciences for Woman, University of Babylon, Hilla 51001, Iraq
(*) Corresponding Author

Abstract


The study focused on producing and examining the properties of the 2-(((3-mercapto-5-(4-nitrophenyl)-4H-1,2,4-triazol-4-yl)imino)methyl)-4-(((4-mercaptophenyl) diazenyl)phenol) ligand (L) and its complexes with three transition metal ions, namely Ni(II), Co(II), and Cu(II). The ligand was formed through diazotization and coupling reactions between 4-aminobenzenethiol and a coupling Schiff base derived from 1,2,4-triazole. The characterization of the ligand and its metal ion complexes was carried out using analytical techniques such as FTIR, 1H- and 13C-NMR, UV-visible spectroscopy, and thermal analysis (TGA and DTG). Various physical methods were employed to synthesize and analyze the properties of the three mononuclear Co(II), Ni(II), and Cu(II) complexes with the azo-dye Schiff's base ligand. Based on the microanalysis and spectroscopic results, it was determined that the coordination between the azo Schiff base ligand and the central metal ion occurred through the NOS-donating atoms of the ligand. The analysis of the electronic spectra revealed that the synthesized Co(II) and Ni(II) complexes  exhibited an octahedral geometry, while the Cu(II) complex had a distorted octahedral geometry. The implications of the finding regarding the octahedral and distorted-octahedral geometries include expanding the structural diversity in coordination chemistry, providing insights into ligand-metal interactions, and understanding the influence of geometry on properties.

Keywords


azo-dye; Schiff base; metal ion complex; triazol

Full Text:

Full Text PDF


References

[1] İspir, E., 2009, The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes, Dyes Pigm., 82 (1), 13–19.

[2] Alghool, S., Abd El-Halim, H.F., and Dahshan, A., 2010, Synthesis, spectroscopic thermal and biological activity studies on azo-containing Schiff base dye and its cobalt(II), chromium(III) and strontium(II) complexes, J. Mol. Struct., 983 (1-3), 32–38.‏

[3] Sancak, K., Er, M., Ünver, Y., Yildirim, M., Degirmencioglu, I., and Serbest, K., 2007, Cu(II), Ni(II) and Fe(II) complexes with a new substituted [1,2,4] triazole Schiff base derived from 4-amino-5-(thien-2-yl ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-hydroxy-1-naphthaldehyde: Synthesis, characterization and a comparison of theoretical and experimental results by Ab initio calculation, Transition Met. Chem., 32 (1), 16–22.‏

[4] Klingele, M.H., Noble, A., Boyd, P.D.W., and Brooker, S., 2007, Synthesis and X-ray crystal structures of some mononuclear and dinuclear complexes of 4-isobutyl-3,5-di(2-pyridyl)-4H-1,2,4-triazole, Polyhedron, 26 (2), 479–485.‏

[5] Gouda, M.A., Eldien, H.F., Girges, M.M., and Berghot, M.A., 2016, Synthesis and antitumor evaluation of thiophene based azo dyes incorporating pyrazolone moiety, J. Saudi Chem. Soc., 20 (2), 151–157.‏

[6] Yaman, M., İpek Dirin, E., Kaplan, G., Seferoğlu, N., and Seferoğlu, Z., 2022, The synthesis, photophysical properties, DFT study and textile applications of fluorescent azo dyes bearing coumarin-thiazole, J. Mol. Liq., 368, 120718.

[7] Kumari, S., Maddipoti, K., Das, B., and Ray, S., 2019, Palladium–Schiff base complexes encapsulated in zeolite-Y host: Functionality controlled by the structure of a guest complex, Inorg. Chem., 58 (2), 1527–1540.‏

[8] Diaz-Ortiz, A., Prieto, P., Carrillo, J.R., Martin, R., and Torres, I., 2015, Applications of metal-free 1,2,4-triazole derivatives in materials science, Curr. Org. Chem., 19 (7), 568–584.‏

[9] Bazhina, E.S., Bovkunova, A.A., Shmelev, M.A., Korlyukov, A.A., Pavlov, A.A., Hochvaldová, L., Kvítek, L., Panáček, A., Kopel, P., Eremenko, I., and Kiskin, M.A., 2023, Zinc(II) and copper(II) complexes with N-substituted imines derived from 4-amino-1,2,4-triazole: Synthesis, crystal structure, and biological activity, Inorg. Chim. Acta, 547, 121359.‏

[10] Bader, A.T., Al-qasii, N.A.R., Shntaif, A.H., El Marouani, M., Majidi, M.I.H.A., 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.‏

[11] Nonkuntod, P., Senawong, T., Soikum, C., Chaveerach, P., Watwiangkham, A., Suthirakun, S., and Chaveerach, U., 2022, Copper(II) compounds of 4‐nitrobenzohydrazide with different anions (ClO4, NO3 and Br): Synthesis, characterization, DFT calculations, DNA interactions and cytotoxic properties, Chem. Biodiversity, 19 (3), e202100708.‏

[12] Bader, A.T., Rasheed, N.A., Aljeboree, M., and Alkaiml, A.F., 2020, Synthesis, characterization of new 5-(4-nitrophenyl)-4-((4-phenoxybenzylidene)amino)-4H-1,2,4-triazole-3-thiol metal complexes and study of the antibacterial activity, J. Phys.: Conf. Ser., 1664, 012100.

[13] Beyzaei, H., Ghanbari Kudeyani, M., Samareh Delarami, H., and Aryan, R., 2020, Synthesis, antimicrobial and antioxidant evaluation, and molecular docking study of 4,5-disubstituted 1,2,4-triazole-3-thiones, J. Mol. Struct., 1215, 128273.‏

[14] Oderinlo, O.O., Jordaan, A., Seldon, R., Isaacs, M., Hoppe, H.C., Warner, D.F., Tukulula, M., and Khanye, S.D., 2023, Hydrazone‐tethered 5‐(pyridin‐4‐yl)‐4H‐1,2,4‐triazole‐3‐thiol hybrids: Synthesis, characterisation, in silico ADME studies, and in vitro antimycobacterial evaluation and cytotoxicity, ChemMedChem, 18 (6), e202200572.

[15] Almáši, M., Vilková, M., and Bednarčík, J., 2021, Synthesis, characterization and spectral properties of novel azo-azomethine-tetracarboxylic Schiff base ligand and its Co(II), Ni(II), Cu(II) and Pd(II) complexes, Inorg. Chim. Acta, 515, 120064.

[16] Alothman, A.A., Albaqami, M.D., and Alshgari, R.A., 2021, Synthesis, spectral characterization, quantum chemical calculations, thermal studies and biological screening of nitrogen and oxygen donor atoms containing Azo-dye Cu(II), Ni(II) and Co(II) complexes, J. Mol. Struct., 1223, 128984.‏

[17] Piegat, A., Goszczyńska, A., Idzik, T., and Niemczyk, A., 2019, The importance of reaction conditions on the chemical structure of N,O-acylated chitosan derivatives, Molecules, 24 (17), 3047.‏

[18] Hari, S., Swaroop, T.R., Preetham, H.D., Mohan, C.D., Muddegowda, U., Basappa, S., Sethi, G., and Rangappa, K.S., 2020, Synthesis, cytotoxic and heparanase inhibition studies of 5-oxo-1-arylpyrrolidine-3-carboxamides of hydrazides and 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol, Curr. Org. Synth., 17 (3), 243–250.‏

[19] Aggarwal, R., Hooda, M., Kumar, P., and Sumran, G., 2022, Vision on synthetic and medicinal facets of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine scaffold, Top. Curr. Chem., 380 (2), 10.‏

[20] Panda, K.C., Ravi Kumar, B.V.V., and Sahoo, B.M., 2022, Microwave induced synthesis of 1,2,4-triazole derivatives and study of their anthelmintic and anti-microbial activities, Res. J. Pharm. Technol., 15 (12), 5746–5750.‏

[21] Xie, W., Zhang, H., He, J., Zhang, J., Yu, Q., Luo, C., and Li, S., 2017, Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase, Bioorg. Med. Chem. Lett., 27 (3), 530–532.‏

[22] Pavia, D.L., Lampman, G.M., Kriz, G.S., and Vyvyan, J.A., 2014, Introduction to Spectroscopy, 5th Ed., Cengage Learning, Stamford, CT, US.‏

[23] de Araújo, E.L., Barbosa, H.F.G., Dockal, E.R., and Cavalheiro, É.T.G., 2017, Synthesis, characterization and biological activity of Cu(II), Ni(II) and Zn(II) complexes of biopolymeric Schiff bases of salicylaldehydes and chitosan, Int. J. Biol. Macromol., 95, 168–176.‏

[24] Abdel‐Rahman, L.H., Abu‐Dief, A.M., Moustafa, H., and Hamdan, S.K., 2017, Ni(II) and Cu(II) complexes with ONNO asymmetric tetradentate Schiff base ligand: Synthesis, spectroscopic characterization, theoretical calculations, DNA interaction and antimicrobial studies, Appl. Organomet. Chem., 31 (2), e3555.‏

[25] Retnam, C.T.G., Rose, S.V., and Kumari, B.S., 2023, Synthesis, characterization, biological activity and molecular docking study of transition metal complexes from heterocyclic ligand system, J. Mol. Struct., 1282, 135162.

[26] Al Zoubi, W., Al-Hamdani, A.A.S., and Ko, Y.G., 2017, Schiff bases and their complexes: Recent progress in thermal analysis, Sep. Sci. Technol., 52 (6), 1052–1069.‏

[27] Kavitha, N., and Anantha Lakshmi, P.V., 2017, Synthesis, characterization and thermogravimetric analysis of Co(II), Ni(II), Cu(II) and Zn(II) complexes supported by ONNO tetradentate Schiff base ligand derived from hydrazino benzoxazine, J. Saudi Chem. Soc., 21, S457–S466.‏



DOI: https://doi.org/10.22146/ijc.83509

Article Metrics

Abstract views : 1896 | views : 1064


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.

Web
Analytics View The Statistics of Indones. J. Chem.