Synthesis, structural characterization, and catalytic reduction study of Co(II) complex towards toxic organic compounds; nitrophenol, and nitroaniline

Document Type : Original Article

Authors

1 Chemistry Department, Faculty of Science (Girl’s), Al-Azhar University, Youssif Abbas St., Nasr-City, Cairo, Egypt.

2 Chemistry Department, Faculty of Women for Arts, Science, and Education, Ain Shams University, Cairo, Egypt

Abstract

This work demonstrates the synthesis of Co(II) complex of a new imine ligand incorporated sulfonamide, and coumarin moiety. The ligand and its complex were characterized by elemental analysis, IR, 1HNMR, mass, UV-Vis spectroscopy, molar conductance, magnetic susceptibility and thermal gravimetric analysis (TGA-DTG). According to the spectral analysis, the ligand, HL acts as a multidente donor coordinating through NONO donor sites. The Co(II) complex has tetrahedral geometry, and non-electrolytic in nature. The thermodynamic parameters as activation energy, enthalpy of activation, entropy of activation, and free energy of activation were determined via the thermal analysis. Furthermore, the ability of Co(II) complex as a catalyst was examined toward the reduction of nitrophenol, and nitroaniline in presence of NaBH4 as a reducing agent at room temperature. The results achieved in this investigation are valuable, and paves the way to use the metal complexes derived from heterocyclic organic compounds as catalysts for industrial applications.

Keywords

Main Subjects


[1]   Mohammadtaghi V, Shubo D, Giovanni C, Wei W, Pingping M, Dengchao L, Gang Y, Regeneration of chitosan-based adsorbents used in heavy metal adsorption: A review, J. Separation and Purification Technology. 2019; 224: 373–387.
[2]   Hailan Y, Shujing Y, Zhuotong Z, Guangming Z, Xiaofei T, Rong X, Jiajia W, Biao S, Li D, Meng Q, Yuanyuan Y, Fuhang X, Utilization of biochar for resource recovery from water: A review, Chemical Engineering Journal. 2020; 397: 125502.
[3]   Ertugrul E, Maria H, Osman G, Mucahit S, Ali Y, New construction materials synthesized from water treatment sludge and fired clay brick wastes, J. Building Engineering. 2021; 42: 102471.
[4]   Sasireka V, Anurag R, Senthilarasu S, Tapas KM, A Review on Heavy Metal Ions and Containing Dyes Removal Through Graphene Oxide-Based Adsorption Strategies for Textile Wastewater Treatment, J. Chem. Rec. 2021; 21: 1–42.
[5]   Sumei L, Saisai S, Sha C, Hanbing L, Ziyi L, Yixuan L, Jiaying F, Linhua X, Jianrong L, Photocatalytic degradation of hazardous organic pollutants in water by Fe-MOFs and their composites: A review, J. Environmental Chemical Engineering. 2021; 9: 105967.
[6]    Mu J, Yang J, Zhang D, Jia Q, Progress in Preparation of Metal Nanoclusters and Their Application in Detection of Environmental Pollutants, chinese journal of analytical chemistry. 2021; 49: 319–329.
[7]   Kim O, Is the objective of the Water Framework Directive to deal with pollutant emissions at source coherently implemented by the EU’s substance-specific legal acts? A comparison of the environmental risk control of pharmaceutical legislation with the REACH-, Biocidal Products- and Plant Protection Products Regulation, J. Sustainable Chemistry and Pharmacy. 2021; 20: 100386.
[8]   A. Cabrera, C. Torresa S. Marchettib and S. Stewart, Degradation of methylene blue dye under dark and visible light conditions in presence of hybrid composites of nanostructured MgFe2O4 ferrites and oxygenated organic compounds, J. Environmental Chemical Engineering, 2020; 8: 104274.
[9]   Shamim AH, Hu SH, Mohammad Y, Kang HP, Silver nanoparticles deposited on metal tungsten bronze as a reusable catalyst for the highly efficient catalytic hydrogenation/reduction of 4-nitrophenol, J. Catalysis Communications, 2020; 141: 106011.
[10]   Ravi K, Ranjana G, Synthesis of nanocrystallineCuO–ZnO mixed metal oxide powder by a homogeneous precipitation method, J. Ceramics International, 2014; 40: 10919–10926.
[11] Zimin L, Jinsong D, Xingxing J, Pengfei L, Xuefeng J, Jiang Y, Polyurethane/Keratin/AgNPsnanofibrous mats as catalyst support for 4-nitroaniline reduction, J. Materials Letters, 2019; 237: 9–13.
[12] Liu. Y, Yang. L, Yin. D, Dang. Y, Yang. L, Zou.Q and Li. J, Solvent-free synthesis, characterization, biological activity of Schiff bases and their metal (II) complexes derived from ferrocenylchalcone, J. Organomet. Chem. 2019; 899:120903-120909.
[13]  Dara MA, Hashim JA, Synthesis of new ß-lactam- N-(thiazol-2-yl) benzene sulfonamide hybrids: Their in vitro antimicrobial and in silico molecular docking studies, J. Mol. Struct.2020; 1222: 128904.
[14]  Abou-Hussein. A.A, Wolfgang L, Synthesis, spectroscopic studies and inhibitory activity against bactria and fungi of acyclic and macrocyclic transition metal complexes containing a triaminecoumarine Schiff base ligand, J. SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy, 2015; 141: 223–232.
[15] Lian W, Lu L, Xia W, Ming-Lin W, Jin-Ming L, Ru-Song Z, Spherical mesoporous covalent organic framework as a solid-phase extraction adsorbent for the ultrasensitive determination of sulfonamides in food and water samples by liquid chromatography-tandem mass spectrometry, J. Chromatography A, 2020; 1625: 461275.
[16] Syed AT, Muhammad A, Mahmood A, Muhammad I, Riaz H, Mehwish S, Muhammad Y, Muhammad M, Levofloxacin and sulfa drugs linked via Schiffbases: Exploring their urease inhibition, enzyme kinetics and in silicostudies, J. Molecular Structure, 2021; 1235:  130226.
[17]  Diego M. G, Fernando FS, G.A. Echeverría, Oscar EP, Hiram P, Aida A, A detailed exploration of intermolecular interactions in 4-(4 dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis, J. SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy, 2017; 185: 286–297.
[18]  Ahmed AM, Molecular structure and spectroscopic properties of novel manganese(II) complex with sulfamethazine drug, J. Molecular Structure, 2013; 1035: 114–123.
[19] Neelam M, Priyanka D, Prabhakar KV, Anurag K, Design, synthesis, and biological evaluation of thiourea and guanidine derivatives of pyrimidine-6-carboxylate, J. Res ChemIntermed, 2015; 41: 7981–7993.
[20] Saliha A, Ümmühan OO, Sevki A, Hamit A, Esra B, Kerem K, Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiffbases of sulfa drugs, J. Molecular Structure, 2021; 1223: 128911.
[21] Sangamesh AP, Shrishila NU, Ajaykumar DK, Vinod HN, Prema SB, Co(II), Ni(II) and Cu(II) complexes with coumarin-8-yl Schiff-bases: Spectroscopic, in vitro antimicrobial, DNA cleavage and fluorescence studies, J. SpectrochimicaActa Part A, 2011; 79: 1128– 1136.
[22]  Ismail A, Marwa GE, Nashwa M, Novel Synthesized BenzesulfonamideNanosized Complexes; Spectral Characterization, Molecular Docking, Molecular Modeling and Analytical Application, J. Inorg. Organomet. Polym. Mat., 2019; 29: 876–892.
[23]  Peter AA, Gabriel AK, Paul O, Madeleine H, James R, Cobalt(II) complexes of the antibiotic sulfadiazine, the X-ray single crystal structure of [Co(C10H9N4O2S)2(CH3OH)2], J.  InorganicaChimicaActa, 2006; 359: 3111–3116.
[24] Maram TB, Reem MA, Mohamed RS, Laila HA, Synthesis, structural characterization, DFT calculations, biological investigation, molecular docking and DNA binding of Co(II), Ni(II) and Cu(II) nanosized Schiff base complexes bearing pyrimidine moiety, J. Mol. Struct. 2019; 1183: 298-312.
[25] Imane H, Mouna S, Fadila B, Belkacem B, Mhamed B, Hocine M, Sofiane B, A new complex of Zinc (II) with sulfamethoxazole ligand: Synthesis, crystal structure, Hirshfeld surface analysis, thermal properties, DFT calculations and antibacterial/antifungal activities, J. Molecular Structure, 2021; 1244: 130903.
[26] Zahid HC, Moulay HY, Aliasghar J, Taibi BH, Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: Indolenyl sulfonamide derivatives, European journal of Medicinal Chemistry, 2010; 45: 1189-1199.
[27]  Alizadeh. A, Mohammadi. R, Bayat. F and Zhu. L, Proton transfer process in synthesis of 3-acetyl-4-(substituted ethylenyl) coumarins and chromeno[3,4-c]pyridines, J. Tetrahedron 2018; 74: 2085-2091.
[28]  Jayakumar. S, Mahendiran. D, Selvan. D, Rahiman. A, Bis(imidazol-1-yl) methane-based heteroscorpionate metal(II) complexes: Theoretical, antimicrobial, antioxidant, in vitro cytotoxicity and c-Met tyrosine kinase studies, J. Molecular Structure, 2019; 1196: 567-577.
[29] Zeinab HA, Complexation of 4-amino-1,3 dimethyl-2,6 pyrimidine-dione derivatives with cobalt(II) and nickel(II) ions: synthesis, spectral, thermal and antimicrobial studies, J. Coordination Chemistry, 2008; 61: 1696–1709.
[30] Abeer AF, Safaa NA, Zeinab HA, Synthesis and characterization of binary and ternary complexes of Co(II), Ni(II), Cu(II) and Zn(II) ions based on 4-aminotoluene-3-sulfonic acid, J.  Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc., 2013; 105: 109–124.
[31]  Ayman AA, Hemmat AE, Spectral, electrochemical, thermal, DNA binding ability, antioxidant and antibacterial studies of novel Ru(III) Schiff base complexes, J. Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 2014; 124: 404–415.
[32]  Anantharamaiah. P.N, Manasa. K.S, Sunil. K.Y.C, Fabrication of magnetically recoverable and reusable MgFe2O4/Ag3PO4 composite for catalytic reduction of 4-Nitrophenol, J. Solid State Sciences 2020; 106: 106302.
[33] Yoki Y, Dewangga OBA, Zulda AZ, SiO2/NiFe2O4 nanocomposites: Synthesis, characterization and their catalytic activity for 4-nitroaniline reduction, J. Mater. Chem. Phys. 2021; 261: 124243-124251.
[34] Madhusudan KM, Dipanjan S, Suraj K, Himani K, Amita P, N, S doped carbon dots—Plasmonic Au nanocomposites for visible light photocatalytic reduction of nitroaromatics, J. Mater. Res., 2018; 33: 3907-3616.
[35] Tushar KD, Mussel‑inspired Ag/poly(norepinephrine)/MnO2 heterogeneous nanocatalyst for efficient reduction of 4‑nitrophenol and 4‑nitroaniline: an alternative approach, J. Res. Chem. Intermed., 2020; 46: 3629–3650.
[36] Sachin RT, Balu T, Bhaskar SM, Nageshwar DK, Kinetic investigation for the catalytic reduction of nitrophenol using ionic liquid stabilized gold nanoparticles, J. RSC. Adv. 2018; 8: 38384-38391.
[37] Jiangyong L, Jinxing L, Rongfei Y, Xiaodong Y, Lixia W, Panming J, Versatile bifunctional nitrogen-doped porous carbon derived from biomass in catalytic reduction of 4-nitrophenol and oxidation of styrene Chinese, J. Catal. 41 (2020) 1217–1229.