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 Ph2SnCl2, 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