Synthesis, Characterization and Thermal Studies of New Carboxamide Ligand and Co(II), Ni(II), Cu(II) and Fe(II) Metal Complexes Containing Sulfonamide Group

Öz

The new N-carboxamide ligand 2-benzoyl-N-(4-(aminosulfonyl)phenyl)-3-oxo-3-phenylpropanamide (HL) was synthesized from the reaction of dibenzoylacetic acid-Ncarboxyethylamide and sulfonylamide. Then, metal complexes were synthesized from the reaction of ligand with Cu(OAc)2·H2O, Co(OAc)2·4H2O, Ni(OAc)2·4H2O and Fe(OAc)2 metal salts in a 1:2 metal:ligand cytochiometric ratio, respectively. The synthesized carboxamide ligand and its metal complexes were characterized by various techniques such as UV-Vis, FT-IR, NMR, elemental analysis, TGA-DTA.

Anahtar Kelimeler

• Metal complex
• N-Carboxamide ligand
• Characterization
• Thermal Studies

Sülfonamit Grubu İçeren Yeni Karboksamit Ligandı ve Co(II), Ni(II), Cu(II) ve Fe(II) Metal Komplekslerinin Sentezi, Karakterizasyonu ve Termal Çalışmaları

Öz

Yeni N-karboksamit ligandı 2-benzoil-N-(4-(aminosülfonil)fenil)-3-okso-3-fenilpropanamit (HL), dibenzoilasetik asit-N-karboksietilamit ve sülfonilamitin reaksiyonundan sentezlendi. Daha sonra ligandın sırasıyla Cu(OAc)2·H2O, Co(OAc)2·4H2O, Ni(OAc)2·4H2O ve Fe(OAc)2 metal tuzları ile 1:2 metal:ligand sitokiyometrik oranında reaksiyonundan metal kompleksleri sentezlendi. Sentezlenen karboksamid ligandı ve metal kompleksleri, UV-Vis, FT-IR, NMR, elementel analiz, TGA-DTA gibi çeşitli tekniklerle karakterize edildi.

Anahtar Kelimeler

• Metal kompleks
• N-Karboksamit ligand
• Karakterizasyon
• Termal Çalışmalar

Kaynakça

1. Ali A, Ali A, Bakht MA, Ahsan MJ, 2021. Ultrasound promoted synthesis of N-(substituted phenyl)-2-(7‑hydroxy-4-methyl-2H-chromen-2-ylidene)hydrazine-1-carboxamides as cytotoxic and antioxidant agents. Journal of Molecular Structure, 1238: 130452.
2. Belal AAM, El-Deen IM, Farid NY, Zakaria R, Refat MS, 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.
3. Chekkara R, Kandakatla N, Gorla VR, Tenkayala SR, Susithra E, 2017. Theoretical studies on benzimidazole and imidazo[1,2-a]pyridine derivatives as Polo-like kinase 1 (Plk1) inhibitors: Pharmacophore modeling, atom-based 3D-QSAR and molecular docking approach. Journal of Saudi Chemical Society, 21: S311-S321.
4. Dhau JS, Singh A, Brandão P, Felix V, 2021. Synthesis, characterization, X-ray crystal structure and antibacterial activity of bis[3-(4-chloro-N,N-diethylpyridine-2-carboxamide)] diselenide. Inorganic Chemistry Communications, 133: 108942.
5. Fedorova VA, Kadyrova RA, Slita AV, Muryleva AA, Petrova PR, Kovalskaya AV, Lobov AN, Zileeva ZR, Tsypyshev DO, Borisevich SS, Tsypysheva IP, Vakhitova JV, Zarubaev VV, 2022. Antiviral activity of amides and carboxamides of quinolizidine alkaloid (−)-cytisine against human influenza virus A (H1N1) and parainfluenza virus type 3. Natural Product Research, https://doi.org/10.1080/14786419.2019.1696791.
6. Gülcan M, Sönmez M, Berber I. 2012. Synthesis, characterization, and antimicrobial activity of a new pyrimidine Schiff base and its Cu(II), Ni(II), Co(II), Pt(II), and Pd(II) complexes. Turkish Journal of Chemistry, 36: 189-200.
7. Kava HW, Leung WY, Galea AM, Murray V, 2021. The DNA binding properties of 9-aminoacridine carboxamide Pt complexes. Bioorganic & Medicinal Chemistry, 40: 116191.
8. Khademi A, Amiri A, Tirani FF, Schenk-Joß K, 2022. Co(III) carboxamide complexes as electrocatalysts for water splitting. International Journal of Hydrogen Energy, https://doi.org/10.1016/j.ijhydene.2022.03.195.

9. Kiani M, Bagherzadeh M, Meghdadi S, Fadaei-Tirani F, Babaie M, Schenk-Joß K, 2020. Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity. Inorganica Chimica Acta, 506: 119514.
10. Liu J, Liu F, Li Z, Li C, Wu S, Shen J, Wang H, Du S, Wei H, Hou Y, Ding S, Chen Y, 2022. Novel 4-phenoxypyridine derivatives bearing imidazole-4-carboxamide and 1,2,4-triazole-3-carboxamide moieties: Design, synthesis and biological evaluation as potent antitumor agents. Bioorganic Chemistry, 120: 105629.
11. Maravalli PB, Dhumwad SD, Goudar TR, 1999. Synthetic, spectral, thermal and biological studies of lanthanide(III) complexes with a Schiff base derived from 3-N-methylpiperidino-4amino-5mercapto-1,2,4-triazole. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 29: 525–540.
12. Mishra V, Lloret F, Mukherjee R, 2006. Coordination versatility of 1,3-bis[3-(2-pyridyl)pyrazol-1-yl]propane: Co(II) and Ni(II) complexes. Inorganica Chimica Acta, 359: 4053-4062.
13. Neethu KS, Sivaselvam S, Theetharappan M, Ranjitha J, Bhuvanesh NSP, Ponpandian N, Neelakantan MA, Kaveri MV, 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.
14. Öztürkkan Özbek FE, Sertçelik M, Yüksek M, Elmalı A, Şahin E, 2020. The superiority of the classical synthesis compared to the hydrothermal synthesis upon the structural, optical absorption and fluorescent properties of new Cd(II) 3-fluorobenzoate complexes with Pyridine-3-carboxamide/Pyridine-3-carboxylate. Inorganica Chimica Acta, 509: 119694.
15. Panda C, Sarkar A, Gupta SS, 2020. Coordination chemistry of carboxamide ‘Nx’ ligands to metal ions for bio-inspired catalysis. Coordination Chemistry Reviews, 417: 213314. https://doi.org/10.1016/j.ccr.2020.213314.
16. Pokhodylo N, Manko N, Finiuk N, Klyuchivska O, Matiychuk V, Obushak M, Stoika R, 2021. Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents. Journal of Molecular Structure, 1246: 131146.
17. Rambabu G, Kiran YB, Sarveswari S, Vijayakumar V, 2022. Synthesis of New 6-Oxo-1,6-Dihydropyrimidin-5-Carboxamides and Evaluation of Their anti-Bacterial and anti-Oxidant Activities. Polycyclic Aromatic Compounds, https://doi.org/10.1080/10406638.2021.2019799.
18. Ray MS, Bhattacharya R, Chaudhuri S, Righi L, Bocelli G, Mukhopadhyay G, Ghosh A, 2003. Synthesis, characterisation and X-ray crystal structure of copper(II) complexes with unsymmetrical tetradentate Schiff base ligands: first evidence of Cu(II) catalysed rearrangement of unsymmetrical to symmetrical complex. Polyhedron, 22(4): 617-624.
19. Rybalova TV, Krivopalov VP, Gatilov YV, Nikulicheva ON, Shkurko OP, 2007. Supramolecular structure of 6- phenil-2-cloropyrımıdıne-4-carboxamide and its complexes wıth dioxane and ethanol. Journal of Structural Chemistry, 48:318-324.
20. Salib KAR, Saleh AA, El-Wafa SA, El-Shafiy HFO, 2003. Preparation and Characterization of Novel Asymmetrical Schiff-Base Ligands Derived from 2methyl-7-formyl-8-hydroxyquinoline and their Metal Complexes. Journal of Coordination Chemistry, 56(4): 283-298.
21. SathishKumar C, Surendrakumar R, Raman G, Ali D, Alarifi S, Idhayadhulla A, 2022. Bis-(N-aminoethylethanolamine)-Copper(II) nanocatalysis (AEEA-Cu(II)-NPs) meditated to synthesis a series of 2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide derivatives: Characterization of theoretical, computational and evaluation of molecular docking, and cytotoxicity activities. Journal of King Saud University - Science, 34, 3: 101872.
22. Sönmez M, Çelebi M, Berber I, 2010a. Synthesis, spectroscopic and biological studies on the new symmetric Schiff base derived from 2,6-diformyl-4-methylphenol with N-aminopyrimidine. European Journal of Medicinal Chemistry, 45: 1935-1940.
23. Sönmez M, Çelebi M, Levent A, Berber İ, Şentürk Z, 2010b. A new pyrimidine-derived ligand, N-pyrimidine oxalamic acid, and its Cu (II), Co (II), Mn (II), Ni (II), Zn (II), Cd (II), and Pd (II) complexes: synthesis, characterization, electrochemical properties, and biological activity. Journal of Coordination Chemistry, 63, 848-860.
24. Sogukomerogullari HG, 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.
25. Thaker BT, Surati KR, Patel P, Parmar SD, 2006. Synthesis and spectroscopic studies of mononuclear mixed ligand Schiff base complexes of Cu(II) involving conjugated heterocyclic nitrogen base and N-PhOHA or N-PhDHA. Journal of the Iranian Chemical Society, 3: 371-377.
26. Tomar R, Bhattacharya D, Babu SA, 2022. Direct Lactamization of β‐Arylated δ‐Aminopentanoic Acid Carboxamides: En Route to 4‐aryl‐2‐Piperidones, Piperidines, Antituberculosis Molecule Q203 (Telacebec) and its Analogues. Asian Journal of Organic Chemistry, 11(2):230-240.
27. Verma I, Mukhopadhyay N, Sengupta A, Mukherjee R, 2021. Arylamination via ortho-fusion on an azo-appended pyridine carboxamide complex of copper(II). Journal of Organometallic Chemistry, 956: 122121.
28. Zhang J-H, Xie H-X, Li Y, Wang K-M, Song Z, Zhu K-K, Fang L, Zhang J, Jiang C-S, 2021. Design, synthesis and biological evaluation of novel (E)-2-benzylidene-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)hydrazine-1-carboxamide derivatives as α-glucosidase inhibitors. Bioorganic & Medicinal Chemistry Letters, 52: 128413.