Synthesis, Characterization, and Antibacterial Activity of Ni(II), Pd(II), and Pt(II) Complexes with 2-benzoylthiobenzimidazole

  • Karwan Omer Ali Department of Physics, College of Science, Halabja University, Halabja, Kurdistan Region, Iraq
  • Hikmat Ali Mohammad Department of Chemistry, College of Education, Salahaddin University-Erbil, Kurdistan Region,
Keywords: 2-benzoylthiobenzimidazole; Square planar complexes; Ni(II), Pd(II) and Pt(II) complexes; Antibacterial activity, Structural study.

Abstract

The thioester compound of 2-benzoylthiobenzimidazole was prepared by S-acylation of 2-mercaptobenzimidazole with benzoyl chloride and reactions of divalent Ni, Pd, and Pt salts with one equivalent of thioester compound a new complexes were isolated in a high percentage. A tetradentate thioester compound and a bivalent metal complexes were identified by CHNS analysis, IR, magnetic susceptibility, molar conductivity, UV-Vis, and 1H, 13C NMR spectroscopies. The anti-bacterial activity of the thioester compound and the bivalent metal complexes were studied using disk diffusion test method against the bacterial species, Staphylococcus aureus, and Pseudomonas aeruginosa. The divalent metal complexes demonstrated a greater activities compared to thioester compound a lone. Structural analysis showed that 2-benzoylthiobenzimidazole L behaves as a neutral four coordination modes compound and bonds to the bivalent metals cation through two nitrogen, sulfur and oxygen atoms. Our study informed the formation of four-coordinate square planar complexes structure around divalent metal salts of Ni, Pd, and Pt.

References

Al-Fahdawi, A.S. and Alsalihi, E.I. 2018. Synthesis and Characterization of IronII, CobaltII, NickelII, CopperII, and ZincII complexes Using Diphenylmethyl Xanthate Ligand. Aro-The Scientific Journal of Koya University, 6(1), 33-37.
Ali, K.O., Ali, H.M., Gerber, T. and Hosten, E. 2017. Mixed Ligand, Palladium (II) and Platinum (II) Complexes of Tertiary DiphosphineswithS-1H Benzo[d] Imidazole-2-yl Benzothioate. Oriental Journal of Chemistry, 33 (2), 584-592.
Al-Jibori, S.A., Al-Nassiri, I.N., Al-Hayaly, L.J. and Jassim, A.H. 2002. Mixed ligand transition metal complexes of tertiary phosphines and 5-phenyl-l, 3, 4-oxadiazole-2-thione. Transition Metal Chemistry, 27, 191-195.
Alsalihi, E. I. and Al-Fahdawi, A. S. and Meena, B. A. 2017. Synthesis and Characterization of Sodium Diphenylcarbamodithioate Ligand [L] and its Cobalt, Nickel, and Copper Complexes. Aro-The Scientific Journal of Koya University, 5(2), 1-5.
Amin, O.H., Al-Hayaly, L.J., and Al-Jibori S.A. 2004. Heterobimetallic complexes of palladium (II) and platinum (II) bridged by the ligand 5-phenyl-1, 3, 4-oxadiazole-2-thione. Polyhedron, 23, 2013-2020.
Apenysheva, T.E., Pushkareva, K.S., Bolotin, S.N., Frolov, V.Y., Kolokolov, F.A., Gromachevskaya, E.V., Borodavko, A.A. and Kosulina, T.P. 2006. Synthesis and study of copper(II), nickel(II), and cobalt(II) complex compounds with dihydrobenzoxazine derivatives, Russian Journal of General Chemistry, 76, 641-644.
Aziz, A.A., A., Salem, A. N., Sayed, M.A. and Aboaly, M.M. 2012. Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M (II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure, 1010, 130-138.
Barchéchath, S.D., Tawatao, R.I., Corr, M., Carson, D.A. and Cottam, H.B. 2005. Inhibitors of apoptosis in lymphocytes: synthesis and biological evaluation of compounds related to pifithrin-α. Journal of medicinal chemistry, 48(20), 6409-6422.
Bermejo, E., Carballo, R., Castiñeiras, A., Domı́nguez, R., Maichle-Mössmer, C., Strähle, J. and West, D.X. 1999. Synthesis, characterization and antifungal activity of group 12 metal complexes of 2-acetylpyridine-4 N-ethylthiosemicarbazone (H4EL) and 2-acetylpyridine-N-oxide-4 N-ethylthiosemicarbazone (H4ELO). Polyhedron, 18(27), 3695-3702.
Buttrus, N.H., Hussain, A.K. and Talal, A.K. 2003. Synthesis and characterization of new trinuclear palladium (II) and platinum (II) complexes containing Phosphorus-Sulphur ligands. Asian Journal of Chemistry, 15(3), 1617.
Buyukuslu, H., Akdogan, M., Yildirim, G. and Parlak, C. 2010. Ab initio Hartree-Fock and density functional theory study on characterization of 3-(5-methylthiazol-2-yldiazenyl)-2-phenyl-1H-indole. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 75(4), 1362-1369.
Ceylan, Ü., Çapan, A., Yalçın, Ş.P., Sönmez, M. and Aygün, M. 2017. Vibrational spectroscopic and thermo dynamical property studies, Fukui functions, HOMO-LUMO, NLO, NBO and crystal structure analysis of a new Schiff base bearing phenoxy-imine group. Journal of Molecular Structure, 1136, 222-230.
De Graaf, D.C., Alippi, A.M., Antúnez, K., Aronstein, K.A., Budge, G., De Koker, D., De Smet, L., Dingman, D.W., Evans, J.D., Foster, L.J. and Fünfhaus, A. 2013. Standard methods for American foulbrood research. Journal of Apicultural Research, 52(1), 1-28.
Ferenc, W., Osypiuk, D., Sarzyński, J. and Głuchowska, H. 2018. The New Complexes of Selected Transition Metal Ions with a Ligand Formed by Condensation of Isatin with Amino Acid: Spectral, Thermal, and Magnetic Properties. Russian Journal of General Chemistry, 88, 1525-1532.
Geary, W.J. 1971. The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7, 81-122.
Goux, C., Lhoste, P., and Sinou, D. 1994. Palladium (O)-catalyzed alkylation of thiols. Tetrahedron, 50, 10321-10330.
Gupta, K.C. and Sutar, A.K. 2008. Catalytic activities of Schiff base transition metal complexes. Coordination Chemistry Reviews, 254, 1420-1550.
Gupta, S.K. and Pancholi, S.S. 2011. Synthesis and evaluation of antitubercular activity of some thiobenzimidazolyl derivatives. Der Pharma Chemica, 3(1), 274-279.
Gurrala, S., Babu, Y.R., Rao, M.V. and Latha, B.M. 2011. Symmetrical coupling of 2-mercapto Benzimidazole derivatives and their antimicrobial activity. Journal of Pharmacy and Pharmaceutical Sciences, 3(2), 217-220.
Heralagi, R., Jayaveera, I. and Shivkumar, B. 2012. Synthesis of some novel bis type 2-mercapto benzimidazole derivatives. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 3(2), 407-414.
Howlader, M.B., Tarafder, M.T. and Islam, M.A. 2009. Palladium (II) complexes of hydrazones derived from 4-dodecyloxybenzoylhydrazine with some aliphatic and aromatic aldehydes and their mesogenic behaviour. Indian Journal of Chemistry, 48A, 1078-1084.
Huang, W., Zhao, P.L., Liu, C.L., Chen, Q., Liu, Z.M. and Yang, G.F. 2007. Design, Synthesis, and Fungicidal Activities of New Strobilurin Derivatives. Journal of Agricultural and Food Chemistry, 55(8), 3004-3010.
Karaoglu, K., Baran, T., Serbest, K., Er, M. and Degirmencioglu, I. 2009. Two novel macroacyclic schiff bases containing bis-N2O2 donor set and their binuclear complexes: synthesis, spectroscopic and magnetic properties. Journal of Molecular Structure, 922, 39-45.
Kazemi, M. and Shiri, L. 2015. Thioesters synthesis: recent adventures in the esterification of thiols. Journal of Sulfur Chemistry, 36, 613-623.
Khan, S.R.A., Guzman-Jimenez, I., Whitmire, K.H. and Khokhar, A.R. 2000. Synthesis and characterize ation of piperidine platinum (II) complexes with dicarboxylates: crystal and molecular structure of cis-[Pt (piperidine)2Cl2]• H2O. Polyhedron, 19(8), 975-981.
KO, J., Ham, J., Yang, I., Chin, J., Nam, S.J. and Kang, H. 2006. A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes. Tetrahedron Letters, 47, 7101-7106.
Kotovskaya, S.K., Perova, N.M., Baskakova, Z.M., Romanova, S.A., Charushin, V.N. and Chupakhin, O.N. 2001. Fluoro-containing heterocycles. IV. Synthesis of benzimidazole derivatives. Russian Journal of Organic Chemistry, 37(4), 564-569.
Matin, S.J. and Khojasteh, R.R. 2015. Synthesis, characterization, and antibacterial activities of Cr(III), Co(III), Ni(II), and Mn(III) complexes of heptadentate Schiff base ligand derived from tris(2-aminoethyl)amine. Russian Journal of General Chemistry, 85, 1763-1767.
Mavrova, A.T., Vuchev, D., Anichina, K. and Vassilev, N. 2010. Synthesis, antitrichinnellosis and antiprotozoal activity of some novel thieno [2,3-d]pyrimidin-4(3H)-ones containing benzimidazole ring. European Journal of Medicinal Chemistry, 45, 5856-5861.
Mihalache, M., Negreanu-Pirjol, T., Dumitraşcu, F., Drăghici, C. and Călinescu, M. 2018. Synthesis, characterization and biological activity of new Ni (II), Pd (II) and Cr (III) complex compounds with chlorhexidine. Journal of the Serbian Chemical Society, 83(3), 271-284.
Neumann, C.S. and Walsh, C.T. 2008. Biosynthesis of (-)-(1S, 2R)-allocoronamic acyl thioester by an FeII-dependent halogenase and a cyclopropane-forming flavoprotein. Journal of the American Chemical Society, 130(43), 14022-1423.
Okamoto, O., Kobayashi, K., Kawamoto, Ito, H., Satoh, A., Kato, T., Yamamoto, I., Mizutani, S., Hashimoto, M., Shimizu, A. and Sakoh, H. 2008. Identification of novel benzimidazole series of potent and selective ORL1 antagonists. Bioorganic and Medicinal Chemistry Letters, 18, 3278-3281.
Pessoa, J.C., Duarte, M.T., Gillard, R.D., Madeira, C., Matias, P.M. and Tomaz, I. 1998. Preparation of [VO (sal-L-Trp)(H 2 O)](sal-L-Trp= N-salicylidene-L-tryptophanate) and characterisation of an unusual product obtained from its solutions in water pyridine. Journal of the Chemical Society, Dalton Transactions, 23, 4015-4020.
Ramezan, A. A., Ali, M.T., Mohammad, J. H., Khadijeh, M. and Mahdi, G.Z. 2012. A method for antibiotic susceptibility testing: applicable and accurate. Jundishapur Journal of Microbiology, 2012, 341-345.
Rao, S.S., Dubey, P.K. and Kumari Y.B. 2013. A green and simple synthesis of N-substituted-2-mercaptobenzimidazoles. Indian Journal of Chemistry, 52B, 1210-1213.
Sanders, E.R. 2012. Aseptic laboratory techniques: plating methods. Journal of visualized experiments, 63, 3064-3086.
Sauvage, J.P. 1999. Transition Metals in Supramolecular Chemistry. New York: John Wiley.
Schwarzer, D., Ludwig, C., Thiel, I.V. and Mootz, H.D. 2011. Probing intein-catalyzed thioester formation by unnatural amino acid substitutions in the active site. Biochemistry, 51(1), 233-242.
Steed, J.W. and Atwood, J.L. 2000. Supramolecular Chemistry. 2nd ed. New York: John Wiley.
Uçan, S.Y. 2014. Synthesis, Spectral, thermal, and Magnetic Studies of Cobalt(II), Nickel(II), Copper(II), Zinc(II), and Cadmium(II) Complexes With N2O2donor groups. Russian Journal of General. Chemistry, 84, 1819-1824.
Published
2020-04-22
How to Cite
Ali, K. and Mohammad, H. (2020) “Synthesis, Characterization, and Antibacterial Activity of Ni(II), Pd(II), and Pt(II) Complexes with 2-benzoylthiobenzimidazole”, Zanco Journal of Pure and Applied Sciences, 32(2), pp. 15-23. doi: 10.21271/ZJPAS.32.2.3.
Section
Mathematics ,Physics and Engineering Researches