Synthesis, Physical, Chemical and DFT Properties of Cobalt(II), Nickel(II), Copper(II), and Zinc(II) Complexes with Polydentate Schiff Base Derived from 1,2,4-Triazole

https://doi.org/10.22146/ijc.90234

Fatima Haitham Zuhair(1), Zahraa Salim Al-Garawi(2), Mahmoud Najim Al-jibouri(3*), Gehad Genidy Mohamed(4), Abanoub Mosaad Abdallah(5)

(1) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10001, Iraq
(2) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10001, Iraq
(3) Department of Chemistry, College of Science, Mustansiriyah University, Baghdad 10001, Iraq
(4) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt; Nanoscience Department, Basic and Applied Sciences Institute, Egypt-Japan University of Science and Technology, New Borg El Arab, Alexandria 21934, Egypt
(5) Narcotic Research Department, National Center for Social and Criminological Research (NCSCR), Giza 11561, Egypt
(*) Corresponding Author

Abstract


The work describes the synthesis and spectral investigation of cobalt(II), nickel(II), copper(II), and zinc(II) complexes with (E)-4-((4-nitrobenzylidene)amino)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol (L). The new ligand was synthesized through three steps, first the preparation of 3,4,5-trimethoxyphenylhydrazide salt, the ring closure of potassium hydrazide salt with excess of hydrazine hydrate followed by condensation of the derivative 4-amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol with 4-nitrobenzaldehyde in glacial acetic acid. The physical and spectroscopic properties of the ligand and its complexes were well investigated and theoretically studied. The experimental results were compatible with their expected compositions. Based on the spectral data, metal complexes with coordination numbers 6 and 4 were proposed, with L functioning as a bidentate ligand. The metal complexes displayed an octahedral geometry around bivalent cobalt, nickel, and zinc tetrahedral environment. Density functional theory calculations (DFT) were conducted to investigate the geometry optimization of the synthesized ligand L and its Co(II) complex and to confirm the structure of the ligand by comparing its experimental vibrational and NMR spectra with the corresponding DFT calculated spectra. The DFT results revealed the participation of nitrogen and sulfur atoms of imine and thione groups in coordination with the metal ions beside the good agreement with the experimental data of elemental analyses and spectroscopic measurements.


Keywords


1,2,4-triazole complexes; DFT study; polydentate ligand



References

[1] 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.

[2] Galini, M., Salehi, M., Kubicki, M., Amiri, A., and Khaleghian, A., 2017, Structural characterization and electrochemical studies of Co(II), Zn(II), Ni(II) and Cu(II) Schiff base complexes derived from 2-((E)-(2-methoxyphenylimino)methyl)-4-bromophenol; Evaluation of antioxidant and antibacterial properties, Inorg. Chim. Acta, 461, 167–173.

[3] Zafar, W., Sumrra, S.H., and Chohan, Z.H., 2021, A review: Pharmacological aspects of metal based 1,2,4-triazole derived Schiff bases, Eur. J. Med. Chem., 222, 113602.

[4] 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.L., 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.

[5] Bader, A.T., Al-Qasii, N.A.R., Shntaif, A.H., El Marouani, M., AL Majidi, M.I.H., Trif, L., and Boulhaoua, M., 2021, 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.

[6] Ibrahim, M.M., Fathy, A.M., Al-Harbi, S.A., and Ramadan, A.E.M.M., 2021, Triazole based copper(II) complexes: Synthesis, spectroscopic characterization, density function theory study, and biomimicking of copper containing oxidase proteins, J. Chin. Chem. Soc., 68 (8), 1496–1513.

[7] Kamboj, V.K., Verma, P.K., Dhanda, A., and Ranjan, S., 2015, 1,2,4-Triazole derivatives as potential scaffold for anticonvulsant activity, Cent. Nerv. Syst. Agents Med. Chem., 15 (1), 17–22.

[8] 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 (1), 012100.

[9] 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.

[10] 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.

[11] Hari, S., Swaroop, T.R., Preetham, H.D., Mohan, C.D., Muddegowda, U., Basappa, S., Vlodavsky, I., 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.

[12] Sabzi, R.E., Nikoo, A., Nikzad, Y., Bahram, M., Akbari, K., and Samadi, N., 2012, Synthesis and determination of stability constants of a new bis-1,2,4-triazole ligand for complexation with zinc(II), copper(II) and nickel(II) in acetonitrile, Am. J. Anal. Chem., 3 (6), 437–442.

[13] Timur, İ., Kocyigit, Ü.M., Dastan, T., Sandal, S., Ceribası, A.O., Taslimi, P., Gulcin, İ., Koparir, M., Karatepe, M., and Çiftçi, M., 2018, In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4-dihydro-3H-1,2,4-triazole-3-thiones-Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles, J. Biochem. Mol. Toxicol., 33 (1), e22239.

[14] Al-Mansury, S., Balakit, A.A., Alkazazz, F.F., and Ghaleb, R.A., 2021, Synthesis, antiproliferative and antioxidant activity of 3-mercapto-1,2,4-triazole derivatives as combretastatin A-4 analogues, Pharm. Chem. J., 55 (6), 556–565.

[15] 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.

[16] Panda, K.C., Kumar, B.V.V.R., 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.

[17] Al-qasii, N.A.R., Bader, A.T., and Mosaa, Z., 2023, Synthesis and characterization of a novel azo-dye Schiff base and its metal ion complexes based on 1,2,4-triazole derivatives, Indones. J. Chem., 23 (6), 1555–1566.

[18] Jawad, W.A., Balakit, A.A., Al-Jibouri, M.N.A., Sert, Y., and Obies, M., 2023, Design, synthesis, characterization, antioxidant, antiproliferative activity and molecular docking studies of new transition metal complexes of 1,2,4-triazole as combretastatin A-4 analogues, J. Mol. Struct., 1274 (Part 2), 134437.

[19] Singh, K., Kumar, Y., Puri, P., Sharma, C., and Aneja, K.R., 2012, Synthesis, spectroscopic, thermal and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5-oxo-1,2,4-triazine, Med. Chem. Res., 21 (8), 1708–1716.

[20] Dhanaraj, C.J., and Jebapriya, M., 2020, Metal Schiff base complexes of tridentate antipyrine based ligand: Synthesis, spectral characterisation, image analysis and biological studies, J. Mol. Struct., 1220, 128596.

[21] Gaber, M., El-Ghamry, H.A., and Fathalla, S.K., 2020, Synthesis, structural identification, DNA interaction and biological studies of divalent Mn, Co and Ni chelates of 3-amino-5-mercapto-1,2,4-triazole azo ligand, Appl. Organomet. Chem., 34 (8), e5678.

[22] Abdallah, A.M., Zaki, N.G., El Kerdawy, A.M., Mahmoud, W.H., and Mohamed, G.G., 2023, Coordination behavior of cocaine toward d-block metal ions: Synthesis, spectral analysis, density functional theory (DFT) studies, and chemotherapeutic activity, J. Mol. Struct., 1293, 136301.

[23] Zhan, C.G., Nichols, J.A., and Dixon, D.A., 2003, Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: Molecular properties from density functional theory orbital energies, J. Phys. Chem. A, 107 (20), 4184–4195.

[24] Hasan, M.M., Md. Ahsan, H., Saha, P., Naime, J., Kumar Das, A., Asraf, M.A., and Nazmul Islam, A.B.M., 2021, Antioxidant, antibacterial and electrochemical activity of (E)-N-(4 (dimethylamino) benzylidene)-4H-1,2,4-triazol-4-amine ligand and its transition metal complexes, Results Chem., 3, 100115.

[25] Ahmed, R.K., OmarAli, A.A.B., Al-Karawi, A.J.M., Marah, S., Jaafar, M.I., Dege, N., Poyraz, E.B., Ozen, T., Loukil, M., Alisir, S.H., and Abdallah, A.M., 2023, Designing of eight-coordinate manganese(II) complexes as bio-active materials: Synthesis, X-ray crystal structures, spectroscopic, DFT, and molecular docking studies, Polyhedron, 244, 116606.

[26] Wolinski, K., Hinton, J.F., and Pulay, P., 1990, Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations, J. Am. Chem. Soc., 112 (23), 8251–8260.

[27] Ali, G.Q., El-Hiti, G.A., Tomi, I.H.R., Haddad, R., Al-Qaisi, A.J., and Yousif, E., 2016, Photostability and performance of polystyrene films containing 1,2,4-triazole-3-thiol ring system Schiff bases, Molecules, 21 (12), 1699.

[28] Ahmed, R.K., OmarAli, A.A.B., Al-Karawi, A.J.M., Marah, S., Jaafar, M.I., Dege, N., Poyraz, E.B., Ozen, T., Loukil, M., Alisir, S.H., and Abdallah, A.M., 2023, Designing of eight-coordinate manganese(II) complexes as bio-active materials: Synthesis, X-ray crystal structures, spectroscopic, DFT, and molecular docking studies, Polyhedron, 244, 116606.

[29] Al-Garawi, Z.S., Abdallah, A.M., Sabah, R.S., Al-jibouri, M.N., Tbatbaei, Z.M.A., and Mohamed, G.G., 2023, Design, DFT and molecular doping studies of metal complexes as a neurotransmitter modulator of autism spectrum disease in preschool children, J. Mol. Struct., 1290, 135875.

[30] Abdallah, A.M., Gomha, S.M., Zaki, M.E.A., Abolibda, T.Z., and Kheder, N.A., 2023, A green synthesis, DFT calculations, and molecular docking study of some new indeno[2,1-b]quinoxalines containing thiazole moiety, J. Mol. Struct., 1292, 136044.



DOI: https://doi.org/10.22146/ijc.90234

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