Abstract

Organotin (IV) carboxylates with the general formulae R2Sn(Cl)L [R = Me (1), n-Bu (2), Ph (3)] and R3SnL [R = Me (4), Ph (5)] have been synthesized by the reaction of 4-piperidinecarboxylic acid (HL) with KOH and R2SnCl2 (R = Me, n-Bu, Ph)/R3SnCl (R = Me, Ph) in methanol under stirring conditions. The metal ligand binding site, structure, and stability of complexes have been verified by FT-IR, (1H, 13C) NMR, EI-MS technique, and semiempirical study. The FT-IR data indicate the bidentate chelating mode of the carboxylate ligand which is also confirmed by semiempirical study. In solution state, five and four coordinated geometry around tin was confirmed by NMR spectroscopy. The EI-MS data agreed well with the molecular structure of the complexes. Thermodynamic parameters and molecular descriptors were calculated by using semiempirical PM3 method. HOMO-LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack as compared to triorganotin complexes. Computed negative heat of formation indicates that complexes 1–4 are thermodynamically stable. The organotin(IV) carboxylates displayed powerful antimicrobial activities against various strains of bacteria and fungi and their minimal inhibitory concentration were also evaluated. The complexes exhibited comparatively higher hemolytic activity as compared to free ligand.

Highlights

  • Organotin complexes are subject of great interest due to their structural diversities and broad range of applications in various fields [1]

  • Keeping in view the great importance of organotin chemistry and in continuation of our previous work [15,16,17], we report here the synthesis, characterization, semiempirical study, and biological activities of organotin carboxylates with 4-piperidinecarboxylic acid

  • Infrared spectra of the organotin(IV) complexes provide valuable information regarding the structure of compounds and coordination geometry of the metal in the solid state

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Summary

Introduction

Organotin complexes are subject of great interest due to their structural diversities and broad range of applications in various fields [1]. Organotin(IV) carboxylates possess significant properties as antibacterial and antifungal agents and as antitumor and anticancer drugs [7]. The antifungal, antibacterial, and antitumor activities of organotin(IV) carboxylates are essentially related to the number and nature of the organic groups attached to the central Sn atom [8]. Triorganotin(IV) compounds display better biological activity than their diorganotin and monoorganotin analogs. This has been attributed to their ability to bind proteins [9]. The synthesis of organotin complexes in research area is of increased interest for inorganic, pharmaceutical, and medicinal chemistry as an approach to the development of new drugs [11, 12]

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