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Chemical Papers

, Volume 72, Issue 4, pp 903–919 | Cite as

Synthesis, spectroscopic characterization, X-ray structure, DFT calculations, and antimicrobial studies of diorganotin (IV) complexes of monotopic oxygen nitrogen donor Schiff base

  • Shaukat Shujah
  • Saqib Ali
  • Nasir Khalid
  • Mohammad Jane Alam
  • Shabbir Ahmad
  • Auke Meetsma
Original Paper
  • 98 Downloads

Abstract

Seven new diorganotin(IV) complexes, [Me2SnL] (1), [Et2SnL] (2), [(n-Bu2SnL] (3), [Ph2SnL] (4), [(n-Oct2SnL] (5), [tert-Bu2SnL] (6), and [n-BuClSnL] (7) have been synthesized from the reaction of N′-(2-hydroybenzylidene)-4-tert-butylbenzohydrazide (H2L) with the corresponding diorganotin(IV) dichloride/oxide or organotin(IV) chloride dihydroxide. The synthesized compounds were structurally characterized by FT-IR, multinuclear NMR (1H and 13C) spectroscopies, elemental analysis, mass spectrometry, DFT/(B3LYP) calculations, and, for ligand single crystal, X-ray diffraction analysis. Spectroscopic evidence affirms coordination of ligand to the dialkyltin(IV) moieties through oxygen nitrogen donor sites in iminol form. The 1 J(119Sn, 13C) coupling constants, 584-655 Hz and 2 J(119Sn-1H) coupling constant, 79 Hz for complex (1), suggest pentacoordination around Sn atom in solution. Single-crystal X-ray structure of ligand show its existence in amido form. Supramolecular architecture mediated by N(2)-H···O(2) and C-H…π interactions is formed in solid state. The DFT calculations have been performed to obtain various structure-based molecular properties as well as to support experimental results. The synthesized compounds were screened in vitro against various human pathogenic microbial strains. Escherichia coli and Staphylococcus aureus were most visibly inhibited by complexes (4) and (7). Highest antifungal activity was shown by compound (6) against Fusarium solani. Compound (3) displayed highest cytotoxicity among synthesized compounds with LD50 0.44μg/mL.

Graphical Abstract

Keywords

Diorganotin(IV) complexes DFT calculations Antibacterial activity Antifungal Activity Cytotoxicity 

Notes

Acknowledgements

The authors are thankful to Higher Education Commission of Pakistan for the financial support.

Supplementary material

11696_2017_333_MOESM1_ESM.docx (7.5 mb)
Supplementary material: CCDC reference number 993525 contains the supplementary crystallographic data for N′-(2-hydroxybenzylidene)-4-tert-butylbenzohydrazide (H2L). These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.ac.uk/data_request/cif. Electronic Supplementary Material associated with this article can be found in the online version of this paper (DOI: xxxxxxxxxx) (DOCX 7686 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2017

Authors and Affiliations

  1. 1.Department of ChemistryKohat University of Science and TechnologyKohatPakistan
  2. 2.Department of ChemistryQuaid-i-Azam UniversityIslamabadPakistan
  3. 3.Chemistry DivisionPakistan Institute of Nuclear Science and TechnologyIslamabadPakistan
  4. 4.Department of PhysicsAligarh Muslim UniversityAligarhIndia
  5. 5.Chemical Physics, Crystal Structure Center, Zernike Institute for Advanced MaterialsUniversity of GroningenGroningenThe Netherlands

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