Synthesis and Characterization of s-Triazine Cored Schiff Base Containing β-lactam and Its [M(Salen/Saloph)] (M= Cr3+ and Fe3+) Capped Complexes

Year 2024, , 73 - 79, 01.10.2024

Ahmet Caymaz Ahmed Hamdi Mirghani , Şaban Uysal

https://doi.org/10.35238/sufefd.1490910

Abstract

This study consists of a tripodal 6-iminopenicylanic acid ligand synthesized based on the s-triazine group and its four trinuclear complexes. For this purpose, 2,4,6-tri(p-formylphenoxy)-1,3,5-triazine (III) (TRIPOD) was obtained from the reaction of 2,4,6-trichloro-1,3,5-triazine and 4-hydroxybenzaldehyde. Then, tripodal target ligand (V) was obtained from the reaction of TRIPOD and 6-aminopenicylanic acid. Finally, tripodal trinuclear (ML) capped target complexes were obtained from the reactions of the initial complexes [(ML)2O] (M= Cr3+ or Fe3+, L= Salen or Saloph) with the target ligand in methanol media. The structures of all obtained ligands were elucidated using 1H NMR, FT-IR, and elemental analysis methods. The structures of the complexes were characterized using FT-IR, magnetic susceptibility, ICP-OES, and TGA methods.

Keywords

6-APA, s-triazine, salen, saloph, metal complexes

Ethical Statement

The authors declare that there is no conflict of interest related to this work.

Supporting Institution

Karabük Üniversitesi Bilimsel Araştırma Projeleri Fonu

Project Number

KBUBAP-21-YL-082

Thanks

We acknowledge that this study was financially supported by the Karabuk University Scientific Research Projects Coordinatorship (Project No: KBUBAP-21-YL-082).

β-laktam İçeren s-Triazin Merkezli Schiff Bazı ve Onun [M(Salen/Saloph)] (M= Cr3+ ve Fe3+) Başlıklı Komplekslerinin Sentezi ve Karakterizasyonu

Abstract

Bu çalışma, s-triazin grubu ve onun dört trinükleer kompleksine dayalı olarak sentezlenen tripodal 6-iminopenisilanik asit ligandından oluşmaktadır. Bu amaçla 2,4,6-trikloro-1,3,5-triazin (III) (TRIPOD) ve 4-hidroksibenzaldehitin reaksiyonundan 2,4,6-tri(p-formilfenoksi)-1,3,5- triazin elde edildi. Daha sonra TRIPOD ve 6-aminopenisilanik asitin reaksiyonundan tripodal hedef ligandı (V) elde edildi. Son olarak, başlangıç komplekslerinin [(ML)2O] (M= Cr3+ veya Fe3+, L= Salen veya Saloph) metanol ortamında hedef ligand ile reaksiyonlarından tripodal trinükleer (ML) başlıklı hedef kompleksleri elde edildi. Elde edilen tüm ligandların yapıları 1H NMR, FT-IR ve elementel analiz yöntemleri kullanılarak aydınlatıldı. Komplekslerin yapıları FT-IR, manyetik duyarlılık, ICP-OES ve TGA yöntemleri kullanılarak karakterize edildi.

Keywords

6-APA, s-triazine, salen, saloph, Metal kompleksleri

Project Number

KBUBAP-21-YL-082

References

• Agathian, K., Kannammal, L., Meenarathi, B., Kailash, S. and Anbarasan, R., (2018), Synthesis, characterization and adsorption behavior of cotton fiber based Schiff base, Int. J. Biol. Macromol., 107, 1102-1112.
• Aouled, I. M. and Uysal, S., (2023), Investigation of thermal and magnetic properties of [MSalen/Saloph](M= Cr3+, Fe3+ or Co3+) capped dinuclear complexes of two novel tetraoxocalix [2] arene [2] triazine ligands, J. Mol. Struc., 1280, 135084.
• De Hoog, P., Gamez, P., Driessen, W. L. and Reedijk, J., (2002), New polydentate and polynucleating N-donor ligands from amines and 2,4,6-trichloro-1,3,5-triazine, Tetrahedron Lett., 43 (38), 6783-6786.
• Hacıoglu, C., (2014), Antibiyotik üretiminde kilit unsur olan 6-APA sentezi için katalitik kriyojel kolonlar, Anadolu University (Turkey).
• Isci, B. and Uysal, S., (2018), The synthesis and characterization of [M (salen/salophen/saldeta)][M= Cr (III), Mn (III) or Fe (III)] capped s-triazine cored tripodal trinuclear Schiff bases complexes, J. Incl. Phenom. Macrocycl. Chem., 92, 281-299.
• Kiymaz, K. and Uysal, S., (2023), The synthesis and characterization of pyridine cored dentrimeric s-Triazine Schiff bases: Investigation of their [MSalen/Salophen](M= Cr3+, Fe3+, Co3+ and Zr4+) capped complexes, J. Mol. Struct., 1271, 134029.
• Koc, Z. E., (2011), Complexes of iron (III) and chromium (III) salen and salophen Schiff bases with bridging 1,3,5‐triazine derived multidirectional ligands, J. Heterocycl. Chem., 48 (4), 769-775.
• Kopel, P., Sindelar, Z. and Klicka, R., (1998), Complexes of iron (III) salen and saloph Schiff bases with bridging dicarboxylic and tricarboxylic acids, Transition Met. Chem., 23, 139-142.
• Mahamoud Aouled, I. and Uysal, S., (2021), Investigation of [MSalen/salophen](M= Cr3+, Fe3+ or Co3+) capped dinuclear complexes of two novel tetraoxocalix[2](m-hydroxymethyl) arene [2] triazine compounds, Synth. Commun., 51 (23), 3642-3655.
• Shiju, C., Arish, D., Bhuvanesh, N. and Kumaresan, S., (2015), Synthesis, characterization, and biological evaluation of Schiff base–platinum (II) complexes, Spectrochim. Acta, Part A, 145, 213-222.
• Srinivas, K., Srinivas, U., Rao, V. J., Bhanuprakash, K., Kishore, K. H. and Murty, U., (2005), Synthesis and antibacterial activity of 2,4,6-tri substituted s-triazines, Bioorg. Med. Chem. Lett., 15 (4), 1121-1123.
• Tahmassebi, D. C. and Sasaki, T., (1994), Synthesis of a new trialdehyde template for molecular imprinting, J. Org. Chem., 59 (3), 679-681.
• Uysal, S. and Ucan, H. I., (2009), The synthesis and characterization of melamine based Schiff bases and its trinuclear [salen/salophenFe(III)] and [salen/salophenCr(III)] capped complexes, J. Incl. Phenom. Macrocycl. Chem., 65, 299-304.
• Uysal, S. and Koc, Z. E., (2010), Synthesis and characterization of dendrimeric melamine cored [salen/salophFe (III)] and [salen/salophCr (III)] capped complexes and their magnetic behaviors, J. Hazard. Mat., 175 (1-3), 532-539.
• Uysal, S. and Koc, Z. E., (2018), 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, J. Mol. Struct., 1165, 14-22.
• Wu, J.-N., Chen, L., Fu, T., Zhao, H.-B., Guo, D.-M., Wang, X.-L. and Wang, Y.-Z., (2018), New application for aromatic Schiff base: High efficient flame-retardant and anti-dripping action for polyesters, Chem. Eng. J., 336, 622-632.
• Yabalak, E., Dondas, H. A. and Gizir, A. M., (2017), Subcritical water oxidation of 6-aminopenicillanic acid and cloxacillin using H2O2, K2S2O8, and O2, J. Environ. Sci. Health., Part A, 52 (3), 210-220.
• Yuste, C., Canadillas-Delgado, L., Labrador, A., Delgado, F. S., Ruiz-Perez, C., Lloret, F. and Julve, M., (2009), Low-dimensional Copper (II) Complexes with the trinucleating ligand 2,4,6-tris(di-2-pyridylamine)-1,3,5-triazine: Synthesis, crystal structures, and magnetic properties, Inorg. Chem., 48 (14), 6630-6640.