The Synthesis of Novel Heterocyclic Schiff Bases Microwave Assisted and Investigation of Saldeta/Salpyr Metal Complexes

Year 2024, , 592 - 598, 31.12.2024

Ziya Erdem Koç

https://doi.org/10.47112/neufmbd.2024.68

Abstract

2-(4-aminophenyl)-1H-benzimidazole obtained from literature studies was used as the outlet agent. The resulting compound reacted with Gentisaldehyde to get 2-(((4-(1H-benzoimidazoleyl)phenyl)imino)methyl)benzene-1,4-diol (25SAPBZ). Oxygen-bridging complexes were obtained by adding the [Fe(saldeta/salpyr)Cl] complex dissolved in ethanol to the (25SAPBZ) ligand. FTIR, elemental analyses, 1H/13C-NMR and FTIR of complex structures, elemental analyses, and magnetic susceptibility measurements of the obtained ligands were elucidated.

Keywords

Heterocyclic, Benzimidazole, Schiff base, Metal Complexes

Mikrodalga Destekli Yeni Heterosiklik Schiff Bazlarının Sentezi ve Saldeta/Salpyr Metal Komplekslerinin İncelenmesi

Abstract

Literatür çalışmalarından elde edilen 2-(4-aminofenil)-1H-benzimidazol çıkış maddesi olarak kullanıldı. Elde edilen bileşik Gentisaldehyde reaksiyona girerek, 2-(((4-(1H-benzimidazolyl)phenyl)imino)methyl)benzene-1,4-diol (25SAPBZ) elde edildi. (25SAPBZ) ligandına etanolde çözülmüş [Fe(saldeta/salpyr)Cl] kompleksi ilave edilerek oksijen köprülü kompleksler elde edildi. Elde edilen ligandların FTIR, elementel analizleri, 1H/13C-NMR ve kompleks yapıların FTIR, elementel analizleri, manyetik süssebtibilite ölçümleri ile yapılar aydınlatıldı.

Keywords

Heterosiklik, Benzimidazol, Schiff baz, Metal Kompleks

References

• Z.E. Koç, Complexes of iron(III) and chromium(III) salen and salophen Schiff bases with bridging 1,3,5‐triazine derived multidirectional ligands, Journal of Heterocyclic Chemistry. 48 (2011), 769–775. doi:10.1002/jhet.577
• N.N. Makhova, L.I. Belen’kii, G.A. Gazieva, I.L. Dalinger, L.S. Konstantinova, V.V. Kuznetsov, A.N. Kravchenko, M.M. Krayushkin, O.A. Rakitin, A.M. Starosotnikov, L.L. Fershtat, S.A. Shevelev, V.Z. Shirinian, V.N. Yarovenko, Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems, Russian Chemical Reviews. 89 (2019), 55–124. doi:10.1070/rcr4914
• P. Arora, V. Arora, H. Lamba, D. Wadhwa, Importance of heterocyclic chemistry: A review, International Journal of Pharmaceutical Sciences and Research. 2012 (2012). doi:10.13040/ijpsr.0975-8232.3(9).2947-54
• S.C. Celik, H. Vatansev, Z.E. Koc, Benzimidazole Schiff bases microwave assisted synthesis and the effect on leukemia cells with flow cytometry, Revue Roumaine De Chimie. 64 (2019) 615–623. doi:10.33224/rrch/2019.64.7.08
• C. Arslaner, S. Karakurt, Z.E. Koc, Synthesis of benzimidazole Schiff base derivatives and cytotoxic effects on colon and cervix cancer cell lines, Biointerface Research in Applied Chemistry. 7(4) (2017), 2103-2107
• Z.E. Koc, H. Bingol, A.O. Saf, E. Torlak, A. Coskun, Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies, Journal of Hazardous Materials. 183 (2010), 251–255. doi:10.1016/j.jhazmat.2010.07.018
• F. Jian, P. Zhao, Y. Li, X. Wang, Q. Yu, A combined computational and experimental approach for investigating a hydrogen‐bonded supermolecular compound comprising benzimidazole and malonic acid, International Journal of Quantum Chemistry. 108 (2007), 521–531. doi:10.1002/qua.21511
• Y. Wei, Y. Yu, K. Wu, Highly Stable Five-Coordinated Mn(II) polymer [Mn(Hbidc)]n (Hbidc=1H-Benzimidazole-5,6-dicarboxylate): Crystal structure, antiferromegnetic property, and strong long-lived luminescence, Crystal Growth & Design. 8 (2008), 2087–2089. doi:10.1021/cg800333g
• Ş. Uysal, Z.E. Koç, Synthesis and characterization of dendrimeric melamine cored [salen/salophFe(III)] and [salen/salophCr(III)] capped complexes and their magnetic behaviors, Journal of Hazardous Materials. 175 (2009), 532–539. doi:10.1016/j.jhazmat.2009.10.038
• M.A. Phillips, The formation of 2-substituted benziminazoles, Journal of the Chemical Society. (1928), 2393–2399. doi:10.1039/jr9280002393
• Z.E. Koc, H.I. Ucan, Complexes of iron(III) salen and saloph Schiff bases with bridging 2,4,6-tris(2,5-dicarboxyphenylimino-4-formylphenoxy)-1,3,5-triazine and 2,4,6-tris(4-carboxyphenylimino-4′-formylphenoxy)-1,3,5-triazine, Transition Metal Chemistry. 32 (2007), 597–602. doi:10.1007/s11243-007-0213-7
• Ş. Uysal, Z.E. Koç, The synthesis and characterization of (MSalen/salophen/saldeta/salpy) [M=Fe(III) or Cr(III)] capped heteromultinuclear schiff bases-dioxime Ni(II) complexes: Their thermal and magnetic behaviours, Journal of Molecular Structure. 1165 (2018), 14–22. doi:10.1016/j.molstruc.2018.03.101
• G. Guney, Z.E. Koc, Investigation of dipodal acetoguanamine-Schiff bases and their homonuclear Fe III complexes, Journal of Coordination Chemistry. 76 (2023), 1679–1695. doi:10.1080/00958972.2023.2262717
• A. Ozer, D.E. Yasa, D.H. Sahin, H. Turbayindir, E. Pehlivan, Z.E. Koc, Investigation of microwave assisted synthesis of Schiff Base derived Metal-Chelates by liquid invert sugar containing D-Glucose, Inorganic and Nano-Metal Chemistry. (2023) 1–12. doi:10.1080/24701556.2023.2197885
• Ş. Uysal, Z.E. Koç, Ş. Çelikbilek, H.İ. Uçan, Synthesis of star-shaped macromolecular Schiff base complexes having Melamine cores and their magnetic and thermal behaviors, Synthetic Communications. 42 (2011), 1033–1044. doi:10.1080/00397911.2010.535635
• P. Kopel, Z. Sindelar, M. Biler, R. Klicka, Complexes of iron(III) salen and saloph Schiff bases bridged by dicarboxylic acids, Polish Journal of Chemistry. 72(9) (1998), 2060-2066
• M. Gembický, R. Boča, F. Renz, A heptanuclear Fe(II)–Fe(III)6 system with twelve unpaired electrons, Inorganic Chemistry Communications. 3 (2000), 662–665. doi:10.1016/s1387-7003(00)00160-x