Synthesis, Characterization, and Antibacterial Activity of Diorganotin(IV) Complexes of 4-Methylphenol

Abstract

Diorganotin(IV) complexes R₂Sn(OC₆H₄Me-4)₂ (R = Ph, Me, and n-Bu) have been synthesized in good yields by the reaction of Ph₂SnCl_2, n-Bu₂SnCl₂, and Me₂SnCl₂ with NaOC₆H₄Me-4, while complex n-Bu₂SnCl(OC₆H₄Me-4) has been obtained from the reaction of n-Bu₂SnCl₂ with 4-methylphenol in the presence of triethylamine in carbon tetrachloride. The complexes have been characterized by elemental analyses, molar conductance measurements, molecular weight determination, IR, ¹H, ¹³C, and ¹¹⁹Sn NMR spectroscopy as well as by mass spectrometry. The reactions of the complexes with 2- and 3-cyanoanilines yielded 1:2 coordination compounds authenticated by physicochemical as well as by IR, ¹H, and ¹³C NMR spectroscopic data. The bases behaved as monodentate ligands wherein 2-cyanoaniline is bonded through nitrile nitrogen atom, while 3-cyanoaniline is coordinated through amino nitrogen atom. The diorganotin(IV) complexes have also been screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus, Staphylococcus epidermidis, Shigella flexneri, Proteus mirabilis, and Pseudomonas aeruginosa. The minimum inhibitory concentration values of these complexes show enhanced activity.

[Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Scheme S1, S2, and Table S1]

GRAPHICAL ABSTRACT

Keywords:

• Dialkyltin/diaryltinchlorides
• 4-methylphenol
• spectral studies
• antibacterial activity

Acknowledgments

Vijay Kumar is grateful to CSIR New Delhi, India, for awarding JRF. The authors thank the Department of Biotechnology, Himachal Pradesh University, Shimla, for providing laboratory facilities (for antibacterial activity), the Department of Science and Technology (DST), Government of India, New Delhi, for providing financial assistance for FT-IR, Sophisticated Analytical Instrument Facility (SAIF), CDRI, Lucknow, for recording mass spectra and elemental analysis, and the Punjab University Chandigarh for recording NMR spectra.