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Synthesis, structural characterization and biological activities of organotin(IV) complexes with 5-allyl-2-hydroxy-3- methoxybenzaldehyde-4-thiosemicarbazone

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Abstract

The organotin(IV) complexes [MeSnCl(L)] (2), [BuSnCl(L)] (3), [PhSnCl(L)] (4) and [Me2Sn(L)] (5) were synthesized by reacting organotin(IV) chloride(s) with 5-allyl-2-hydroxy-3-methoxybenzaldehyde-4-thiosemicarbazone [H2L], (1)] in presence of KOH in 1:2:1 molar ratio (metal salt: base:ligand). All the complexes have been characterized by elemental analyses, UV-Vis, FT-IR, 1H, 13C and 119Sn NMR spectral studies. The molecular structure of complex 5 has been confirmed by single crystal X-ray diffraction analysis. The ligand, H2L coordinates to Sn(IV) in thiolate form through phenoxide-O, azomethine-N and thiolate-S atoms. The C-Sn-C angle measured from coupling constant 1 J(119Sn, 13C) for dimethyltin(IV) complex 5 is 123.4 ∘. The 2 J(119Sn, 1H) coupling constant values for complex 2 and 5 are 72.4 and 76.3 Hz, respectively. Proposed geometry for five coordinated Sn(IV) atom is a strongly distorted trigonal bipyramid. Biological studies were preformed in vitro against four bacterial strains which have shown better activities and potential as antibacterial agents.

Organotin(IV) complexes of 5-allyl-2-hydroxy-3-methoxybenzaldehyde-4-thiosemicarbazone were synthesized and characterized by various physico-chemical methods. Crystal structure of dimethyltin(IV) complex was obtained. Ligand (H2L) acts as dinegative ONS tridentate chelating agent, coordinated to tin(IV) atom via phenolic oxygen, azomethine nitrogen and thiolate sulphur atoms. In vitro antibacterial studies revealed that the complexes possess significant activity.

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Acknowledgment

R.A.H. thanks Universiti Sains Malaysia (USM) for the Research University (RU) Grant 1001/PKIMIA/ 811217. M.A.S. thanks USM and Third World Academy of Sciences (TWAS) for a post-doctoral research fellowship. We also thank the Bangladesh Petroleum Exploration and Production Co. Ltd. (BAPEX), Bangladesh, for the study leave to M. A. Salam.

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  1. The School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    ROSENANI A HAQUE & M A SALAM

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  1. ROSENANI A HAQUE
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  2. M A SALAM
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Correspondence to M A SALAM.

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Supplementary Information

UV-Visible, FT-IR and multinuclear NMR (1H, 13C, and 119Sn) spectra of the ligand and its complexes (figures S1–S9) are available at www.ias.ac.in/chemsci. CCDC reference number 1054928 contains the supplementary crystallographic data for [Me2Sn(L)] (5). This data can be obtained free of charge from the Cambridge Crystallographic data center via www.ccdc.ac.uk/data_request/cif or from the Cambridge Crystallographic data center, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.

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HAQUE, R.A., SALAM, M.A. Synthesis, structural characterization and biological activities of organotin(IV) complexes with 5-allyl-2-hydroxy-3- methoxybenzaldehyde-4-thiosemicarbazone. J Chem Sci 127, 1589–1597 (2015). https://doi.org/10.1007/s12039-015-0924-9

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