Hidrazon Türevi Yeni Fe(II), Co(II), Ni(II) ve Cu(II) Komplekslerinin Sentezi ve Karakterizasyonu

Abstract

2-hidroksinaftaldehit ile nikotinik hidrazit'in kondenzasyon reaksiyonundan N-((2-hidroksinaftalen-1-il)metilen)nikotinohidrazit ligandı elde edilmiştir. N-((2-hidroksinaftalen-1-il)metilen)nikotinohidrazit ligandı ile Fe(II), Co(II), Ni(II) ve Cu(II) asetat tuzlarının (2:1) reaksiyonundan yeni hidrazon metal L2Fe, L2Ni, L2Co ve L2Cu2 kompleksleri sentezlenmiştir. Sentezlenen bileşikler FT-IR, NMR (sadece ligand), UV-Vis, elementel analiz, molar iletkenlik ölçümü, manyetik duyarlılık gibi tekniklerle karakterize edilmiştir. Manyetik duyarlılık ölçümleri L2Fe, L2Co L2Ni ve L2Cu2 kompleksleri için sırasıyla 5.96 BM, 1.03 BM, 1.08 BM ve 1.61 BM olarak kaydedilmiştir. L2Cu2, L2Ni ve L2Co komplekslerinin antiferromanyetik özellikte olduğu belirlenmiştir. L2Fe, L2Co ve L2Ni kompleksleri oktahedral, L2Cu2 kompleksi ise kare düzlem geometriye sahiptir. Komplekslerin molar iletkenlik değerleri 1.31-2.61 μS/cm arasında olup, iletkenlik özelliği taşımamaktadır.

Keywords

• Hidrazon
• Schiff baz
• Metal kompleks
• Karakterizasyon

Synthesis and Characterization of New Hydrazone Derivatives Fe(II), Co(II), Ni(II) and Cu(II) Complexes

Abstract

N-((2-hydroxynaphthalen-1-yl)methylene)nicotinohydrazide ligand derived from the condensation reaction of 2-hydroxynaphthaldehyde and nicotinic hydrazide was obtained. New hydrazone metal complexes L2Fe, L2Co, L2Ni and L2Cu2 were synthesized from the reaction of N-((2-hydroxynaphthalen-1-yl)methylene)nicotinohydrazide ligand and Fe(II), Co(II), Ni(II) and Cu(II) acetate salts in a 2:1 stoichiometric ratio, respectively. The synthesized compounds were characterized by techniques such as FT-IR, NMR (ligand only), UV-Vis, elemental analysis, molar conductivity measurement, magnetic susceptibility. Magnetic susceptibility measurements were recorded as 5.96 BM, 1.03 BM, 1.08 BM and 1.61 BM for the L2Fe, L2Co L2Ni and L2Cu2 complexes, respectively. It has been determined that the L2Cu2, L2Ni and L2Co complexes have antiferromagnetic properties. The L2Fe, L2Co and L2Ni complexes have octahedral geometry, while the L2Cu2 complex has a square plane geometry. The molar conductivity values of the complexes are between 1.31-2.61 μS/cm and do not have conductivity properties.

Keywords

• Hydrazone
• Schiff Base Metal complex
• Characterization

References

1. [1] Rebilly, J. N., Colasson, B., Bistri, O., Over, D., Reinaud, O. 2015. Biomimetic cavity-based metal complexes. Chemical Society Review, 44, 467-489.
2. [2] Shibata, S., Tsuge, K., Sasaki, Y., Ishizaka, S., Kitamura, N. 2015. Directional energy transfer in mixed-metallic copper (I)–Silver (I) coordination polymers with strong luminescence. Inorganic Chemistry, 54, 9733-9739.
3. [3] Maity, T., Saha, D., Bhunia, S., Brandão, P., Das, S., Koner, S. 2015. A family of ligand and anion dependent structurally diverse Cu (II) Schiff-base complexes and their catalytic efficacy in an O-arylation reaction in ethanolic media. RSC Advances, 5, 82179-82191.
4. [4] Zaltariov, M.-F., Vieru, V., Zalibera, M., Cazacu, M., Martins, N. M. R., Martins, L. M. D. R. S., Rapta, P., Novitchi, G., Shova, S., Pombeiro, A.J.L., Arion, V. B. 2017. A Bis(µ-chlorido)-Bridged Cobalt(II) Complex with Silyl-Containing Schiff Base as a Catalyst Precursor in the Solvent-Free Oxidation of Cyclohexane. European Journal of Inorganic Chemistry, 37, 4324-4332.
5. [5] Cao, W., Zheng, X. J., Fang, D. C., Jin, L. P. 2014. A highly selective and sensitive Zn (II) complex-based chemosensor for sequential recognition of Cu (II) and cyanide. Dalton Transactions, 43, 7298-7303.
6. [6] Parsaei, M., Asadi, Z., Khodadoust, S. 2015. A sensitive electrochemical sensor for rapid and selective determination of nitrite ion in water samples using modified carbon paste electrode with a newly synthesized cobalt (II)-Schiff base complex and magnetite nanospheres. Sensors and Actuators B: Chemical, 220, 1131-1138.
7. [7] Wang, Y., Mao, P. D., Wu, W. N., Mao, X. J., Fan, Y. C., Zhao, X. L., Xu, Z. H. 2018. New pyrrole-based single-molecule multianalyte sensor for Cu2+, Zn2+, and Hg2+ and its AIE activity. Sensors and Actuators B: Chemical, 255, 3085-3092.
8. [8] Wang, S., Yang, X., Zhu, T., Bo, L., Wang, R., Huang, S., Chen, H., Jones, R.A. 2018. Construction of luminescent high-nuclearity Zn–Ln rectangular nanoclusters with flexible long-chain Schiff base ligands. Dalton Transactions, 47, 53-57.

9. [9] Yang, Y., Gao, C. Y., Liu, J., Dong, D. 2016. Recent developments in rhodamine salicylidene hydrazone chemosensors. Analytical Methods, 8, 2863-2871.
10. [10] Kumar, A., Lionetti, D., Day, V. W., Blakemore, J. D. 2018. Trivalent Lewis acidic cations govern the electronic properties and stability of heterobimetallic complexes of nickel. Chemistry–A European Journal, 24, 141-149.
11. [11] Dong, W. K., Ma, J. C., Zhu, L. C., Zhang, Y. 2016. Nine self-assembled nickel (II)–lanthanide (III) heterometallic complexes constructed from a Salamo-type bisoxime and bearing a N-or O-donor auxiliary ligand: Syntheses, structures and magnetic properties. New Journal of Chemistry, 40, 6998-7010.
12. [12] Fondo, M., Corredoira-Vázquez, J., Herrera-Lanzós, A., García-Deibe, A. M., Sanmartín-Matalobos, J., Herrera, J. M., Colacio,E., Nuñez, C. 2017. Improving the SMM and luminescence properties of lanthanide complexes with LnO 9 cores in the presence of Zn II: an emissive Zn 2 Dy single ion magnet. Dalton Transactions, 46, 17000-17009.
13. [13] Zhang, J., Xu, L., Wong, W. Y. 2018. Energy materials based on metal Schiff base complexes. Coordination Chemistry Reviews, 355, 180-198.
14. [14] Cao, W., Liu, Y., Zhang, T., Jia, J. 2018. Synthesis, characterization, theoretical and antimicrobial studies of tridentate hydrazone metal complexes of Zn (II), Cd (II), Cu (II) and Co (III). Polyhedron, 147, 62-68.
15. [15] Zülfikaroğlu, A., Ataol, Ç. Y., Çelikoğlu, E., Çelikoğlu, U., İdil, Ö. 2020. New Cu (II), Co (III) and Ni (II) metal complexes based on ONO donor tridentate hydrazone: Synthesis, structural characterization, and investigation of some biological properties. Journal of Molecular Structure, 1199, 127012.
16. [16] Tolan, D. A., Kashar, T. I., Yoshizawa, K., El‐Nahas, A. M. 2021. Synthesis, spectral characterization, density functional theory studies, and biological screening of some transition metal complexes of a novel hydrazide–hydrazone ligand of isonicotinic acid. Applied Organometallic Chemistry, 35(6), e6205.
17. [17] Abdelrahman, M. S. A., Omar, F. M., Saleh, A. A., El-ghamry, M. A. 2021. Synthesis, molecular modeling, and docking studies of a new pyridazinone-acid hydrazone ligand, and its nano metal complexes. Spectroscopy, thermal analysis, electrical properties, DNA cleavage, antitumor, and antimicrobial activities. Journal of Molecular Structure, 131947.
18. [18] Keser Karaoğlan, G. 2022. Synthesis of new Schiff base and its Ni(II), Cu(II), Zn(II) and Co(II) complexes; photophysical, fluorescence quenching and thermal studies. Journal of Molecular Structure, 1256, 132534.
19. [19] El-Sawaf, A. K., El-Essawy, F., Nassar, A. A., El-Samanody, E. A. 2018. Synthesis, spectral, thermal and antimicrobial studies on cobalt (II), nickel (II), copper (II), zinc (II) and palladium (II) complexes containing thiosemicarbazone ligand. Journal of Molecular Structure, 1157, 381-394.
20. [20] Devi, J., Yadav, J., Kumar, D., Jindal, D. K., Basu, B. 2020. Synthesis, spectral analysis and in vitro cytotoxicity of diorganotin (IV) complexes derived from indole-3-butyric hydrazide. Applied Organometallic Chemistry, 34, e5815.
21. [21] Shebl, M., Saleh, A. A., Khalil, S. M., Dawy, M., Ali, A. A. 2021. Synthesis, spectral, magnetic, DFT calculations, antimicrobial studies and phenoxazinone synthase biomimetic catalytic activity of new binary and ternary Cu (II), Ni (II) and Co (II) complexes of a tridentate ONO hydrazone ligand. Inorganic and Nano-Metal Chemistry, 51(2), 195-209.
22. [22] Sarkar, S., Siddiqui, A. A., Saha, S. J., De, R., Mazumder, S., Banerjee, C., Iqbal, M. S., Nag, S., Adhikari, S., Bandyopadhyay, U. 2016. Antimalarial activity of small-molecule benzothiazole hydrazones. Antimicrobial agents and chemotherapy, 60(7), 4217-4228.
23. [23] Carcelli, M., Fisicaro, E., Compari, C., Contardi, L., Rogolino, D., Solinas, C., Stevaert, A., Naesens, L. 2018. Antiviralactivityand metal ion-bindingproperties of some 2-hydroxy-3-methoxyphenyl acylhydrazones. BioMetals, 31(1), 81-89.
24. [24] Sıcak, Y. 2017. Investigation of Antioxidant, Anticholinesterase Inhibitory, Tyrosinase Inhibitory and Urease Inhibitory Activities of Some Hydrazone Derivatives. Türk Yaşam Bilimleri Dergisi, 2(2), 165-170.
25. [25] Mandewale, M. C., Thorat, B., Nivid, Y., Jadhav, R., Nagarsekar, A., Yamgar, R. 2018. Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn (II) complexes. Journal of Saudi Chemical Society, 22(2), 218-228.
26. [26] Abdelrahman, E. M., El‐Shetary, B. A., Shebl, M., Adly, O. M. 2021. Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu (II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies. Applied Organometallic Chemistry, 35(5), e6183.
27. [27] Sıcak, Y. 2018. Synthesis and Characterization of Some New Hydrazones with Anti‐Urease Activities. Journal of Ongoing Chemical Research, 3(2), 71-74.
28. [28] Hijazi, K. A., Taha, Z. A., Ajlouni, A. M., Al-Momani, W. M., Idris, I. M., Hamra, E. A. 2017. Synthesis and biological activities of lanthanide (III) nitrate complexes with N-(2-hydroxynaphthalen-1-yl) methylene) nicotinohydrazide Schiff Base. Medicinal Chemistry, 13(1), 77-84.
29. [29] Maravalli, P.B., Dhumwad, S.D., Goudar, T.R. 1999. Synthetic, spectral, thermal and biological studies of lanthanide(III) complexes with a Schiff base derived from 3-N-methylpiperidino-4-amino-5mercapto-1,2,4-triazole. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 29, 525–540.
30. [30] Soğukömeroğulları, H. G., Taşkın Tok, T., Yılmaz, F., Berber, İ., Sönmez, M. 2015. Synthesis, characterization, biological studies, and molecular modeling of mixed ligand bivalent metal complexes of Schiff bases based on N-aminopyrimidine-2-one/2-thione. Turkish Journal of Chemistry, 39, 497–509.
31. [31] Sönmez, M., Sogukomerogullari, H. G., Öztemel, F., Berber, İ. 2014. Synthesis and biological evaluation of a novel ONS tridentate Schiff base bearing pyrimidine ring and some metal complexes. Medicinal Chemistry Research, 23, 3451–3457.
32. [32] Soğukömeroğullari, H. G., Sönmez, M., Berber, İ. 2016. Synthesis, characterization, antioxidant and antimicrobial studies of Cu(II), Co(II), Ni(II) and Mn(II) complexes with a new Schiff base ligand containing a pyrimidine moiety. International Journal of PharmTech Research, 9 (8), 391-398.
33. [33] Sogukomerogullari, H. G., Sönmez, M., Ceyhan, G. 2019. ONO Tip Schiff Baz Komplekslerinin Sentezi, Karakterizasyonu, Katalitik Özellikleri ve Termal Çalışmaları. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 23(3), 701-708.
34. [34] Belal, A. A. M., El-Deen, I. M., Farid, N. Y., Zakaria, R., Refat, M. S. 2015. Synthesis, spectroscopic, coordination and biological activities of some transition metal complexes containing ONO tridentate Schiff base ligand. Spectrochimica Acta Part A, 149, 771-787.
35. [35] Dede, B., Özen, N., Görgülü, G. 2018. Synthesis, characterization, theoretical calculations and enzymatic activities of novel diimine-dioxime ligand and its homodinuclear Cu(II) complex. Journal of Molecular Structure, 1163, 357-367.
36. [36] Sönmez, M., Şekerci, M. 2003. Synthesis, characterization, and thermal investigation of copper(II), nickel(II), cobalt(II), and zinc(II) complexes with 5-benzoyl-1-(phenylmethylen amino)-4-phenyl1H-pyrimidine-2-thione. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33,1689–1701.
37. [37] Neethu, K.S., Sivaselvam, S., Theetharappan, M., Ranjitha, J., Bhuvanesh, N.S.P., Ponpandian, N., Neelakantan, M.A., Kaveri, M.V. 2021. In vitro evaluations of biomolecular interactions, antioxidant and anticancer activities of Nickel(II) and Copper(II) complexes with 1:2 coordination of anthracenyl hydrazone ligands. Inorganica Chimica Acta, 524, 120419.
38. [38] Sönmez, M., Şekerci, M. 2007. The template synthesis, spectral characterization and thermal behavior of new binuclear Schiff base complexes derived from N-aminopyrimidine with 2, 3-butandion. Journal of the Serbian Chemical Society, 72, 259-264.
39. [39] Goorchibeygi, S., Bikas, R., Soleimani, M., Siczek, M., Lis, T. 2022. Molecular structure and catalytic