Synthesis, Spectroscopic Characterization and in vitro Antibacterial Study of Diorganotin(IV) Complexes of 5-(4-Carboxy-Phenylazo)-2-Hydroxy-Benzoic Acid

Document Type : Research Article

Author

Department of Chemistry, National Institute of Technology, Agartala-799046, West Tripura, INDIA

10.30492/ijcce.2020.38102

Abstract

Diorganotin(IV) complexes [(R2Sn)2HL] [where, R = methyl-, butyl- and L = 5-(4-carboxy-phenylazo)-2-hydroxy-benzoic acid] were synthesized by reacting sodium salt of the ligand [Na2HL] with dimethyl or dibutyltin(IV) dichlorides in anhydrous methanol using2:1 metal-ligand ratio. The complexes were characterized by elemental analysis, UV, IR, 1H, 13C, 119Sn NMR spectroscopy, and Mass spectrometry techniques. The coordination geometry of the complexes was determined using 119Sn NMR spectroscopy and was found to be tetrahedral in the solution state. The molecular mass and the proposed structure of the complexes have been predicted by the molecular ion peaks in the EI-MS spectra of the complexes. The antibacterial activity of the complexes was investigated by screening against different bacteria with respect to the standard drug, Gentamycin.

Keywords

Main Subjects


[1] Tiekink E.R.T., Structural Chemistry of Organotin Carboxylates: A Review of the Crystallographic Literature, Appl. Organomet. Chem.,5(1): 1-23 (1991).
[2] BasuBaul T.S., Singh K.S., Holcapek M., Jirasko R., Rivarola E., Linden A.,  Synthesis, Characterization and Crystal Structures of Polymeric and DimericTriphenyltin(IV) Complexes of 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl] phenyl}methylidene)amino]aryls, J. Organomet. Chem.,690(19): 4232-4242 (2005).
[3] Du D., Jiang Z., Liu C., Sakho A.M., Zhu D., Xu L., MacrocyclicOrganotin(IV) Carboxylates Based on Benzenedicarboxylic Acid Derivatives: Syntheses, Crystal Structures and Antitumor Activities, J. Organomet. Chem., 696(13):2549-2558 (2011).
[5] Tzimopoulos D., Sanidas I., Varvogli A.C., Czapik A., Gdaniec M., Nikolakaki E., Akrivos P.D., On the  Bioreactivity of TriorganotinAminobenzoates. Investigation of Trialkyl and Triaryltin(IV) Esters of 3-Amino and 4- Aminobenzoic Acids, J. Inorg. Biochem.,104(4):423-430 (2010).
[7] Dimertzi D.K., Dokouro V., Primikiri A., Vergas R., Silvestru C., Russo U., Dimertzis M.A.,Organotin Meclofenamic Complexes: Synthesis, Crystal Structures and Antiproliferative Activity of the First Complexes of Meclofenamic Acid – Novel Anti-Tuberculosis Agents, J. Inorg.Biochem.,103(5):738-744 (2009).
[10] Donaldson J.M., Grimes S.M., “Chemistry of Tin, Blackie, London, (1998).
[11] Smith P.J., “Chemistry of Tin, Blackie, London, (1998).
[12] Lickiss P.D., Smith P.J., “Chemistry of Tin, Blackie, London, (1998).
[13] Jastrzebski J.T.B.H., Van G.K., Intramolecular Coordination in Organotin Chemistry, Adv. Organomet. Chem.,35:241-294 (1993).
[18] Roy M., Devi S.S., Roy S., Singh C.B., Singh K.S., Synthesis, Characterization, Crystal Structures and In Vitro Antimicrobial Activities of Triorganotin(IV) Complexes of AzoDicarboxylates, Inorg. Chim. Act. 426: 89-98 (2015).
[19] Tiekink E.R.T., Structural Chemistry of OrganotinCarboxylates: A Review of the Crystallographic Literature, Appl. Organomet. Chem.,5(1): 1-23 (1991).
[20] Ma C., Han Y., Zhang R. Wang D., Self-Assembly of Diorganotin(IV) Moieties and 2-Pyrazinecarboxylic Acid: Syntheses, Characterizations and Crystal, Dalton Trans.,12: 1832-11840 (2004).
[22] Holmes R.R., Organotin cluster chemistry, Acc. Chem. Res.,22(5):190-197 (1989).
[23] Chandrasekhar V., Gopal K., Thilagar P., NanodimensionalOrganostannoxane Molecular Assemblies, Acc. Chem. Res.,40(6): 420-434 (2007).
[24] Eddaoudi M., Moler D.B., Li H., Chen B., Reineke T.M., O’Keeffe M., Yaghi O.M., Modular Chemistry:  Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal-Organic Carboxylate Frameworks, Acc. Chem. Res.,34(4): 319-330 (2001).
[27] Perrin D.D., Armengo W.L.F., “Purification of Laboratory Chemicals, Pergamon, Oxford, (1988).
[28] Reeves D.S., Phillips I., Williams J.D., “Laboratory Methods in Antimicrobial Chemotherapy, Churchill Livingstone, London, (1979).
[29] Kuete V., Fozing D.C., Kapche W.F.G.D., Mbaveng A.T., Kuiate J.R., Ngadjui B.T., Abegaz B.M., Antimicrobial Activity of theMethanolic Extract and Compounds from Morusmesozygia Stem BarkJ. Ethnopharmacol., 124(3):551-555 (2009).
[30] Zgoda J.R., Porter J.R., A Convenient Microdilution Method for Screening Natural Products Against Bacteria and Fungi, Pharm. Biol., 39(3):221-225 (2001).
[31] Kuete V., Ngameni B., Simo C.C.F., Tankea R.K., Ngadim B.T., Meyer J.J.M., Lall N., Kuite R.R., Antimicrobial Activity of the Crude Extracts and Compounds from Ficuschlamydocarpa and Ficuscordata (Moraceae), J. Ethnopharmacol., 120(1):17-24 (2008).
[32] Nath M., Sulaxna, Song X., Organotin(IV) triazolates: Synthesis and Their Spectral Characterization, J. Organomet. Chem.,691(1):  1649-1657 (2006).
[33] Maurya R.M., Jayaswal M.N., Puranik V.G., Chakrabarti P., Gopinathan S., Gopinathan C., Dioxomolybdenum(VI) and Dioxotungsten(VI) Complexes of Isomeric ONO Donor Ligands and the X-ray Crystal Structure of [MoO2(o-OC6H4CH=NCH2C6H4O)(MeOH)]2·MeOH, Polyhedron, 16(1):3977-3983 (1997).
[34]  Chee D.N.A., Affan M.A., Ahmad F.B., Asaruddin M.R., Sam N., Salam M.A., Ismail A., Tan S.H., Synthesis, Characterization, and Antibacterial Activity of Organotin(IV) Complexes with 2-Hydroxyacetophenone Thiocarbohydrazone, J. Coord. Chem., 64(23): 4191-4200 (2011).
[38] Nath M., Saini P.K., Chemistry and Applications of Organotin(IV) Complexes of Schiff Bases, Dalton Trans., 40: 7077-7121 (2011).
[39] Holecek J., Lycka A., Dependence of |1J(119Sn13C)| on the C-Sn-C Angle in n- butyltin(IV) Compounds, Inorg. Chim. Act.,118:L15-L16 (1986).
[41] BasuBaul T.S., Antimicrobial Activity of organotin(IV) Compounds: A Review, Appl. Organomet. Chem., 22(4): 195-204 (2008).