Synthetic, spectroscopic, X-ray structural and antimicrobial studies of 1,3-dithia-2-stibacyclopentane derivatives of phosphorus based dithiolato ligands

Some mixed 1,3-dithia-2-stibacyclopentane derivatives with phosphorus based dithiolato ligands of the types SCH2CH2SS¯bS(S)POGO¯ {where G = CH(Me)CH(Me) and C(Me)2C(Me)2} and SCH2CH2SS¯bS(S)P(OR)2 {where R = Prn, Bun and Ph} have been synthesized by the reaction of 2-chloro-1,3-dithia-2-stibacyclopentane and the ammonium/sodium salt of the corresponding phosphorus based ligands in an equimolar ratio in anhydrous benzene solution. These yellow crystalline solid/semi-solid derivatives have been characterized by elemental analysis (C, H, S and Sb), molecular weights, melting point as well as spectral [UV, IR and NMR (1H, 13C and 31P)] studies. Single crystal X-ray diffraction analyses of 1,3-dithia-2-stibacyclopentane 2,3-butylenedithiophosphate revealed a monodentate mode of bonding of the dithiophosphate ligand in the complex. The free ligands and their antimony(III) complexes have also been screened for their antibacterial and antifungal activities.

Graphical abstractMixed 1,3-dithia-2-stibacyclopentane derivatives with phosphorus based dithiolato ligands of the types SCH2CH2SS¯bS(S)POGO¯ {where G = CH(Me)CH(Me) and C(Me)2C(Me)2} and SCH2CH2SS¯bS(S)P(OR)2 {where R = Prn, Bun and Ph} have been synthesized and characterized by physico-chemical and spectral [UV, IR, NMR (1H, 13C and 31P)] methods. The antimicrobial activities of these complexes were found in vitro against a number of microorganisms by the disc diffusion method and they were found to be better antimicrobial agents than the tested standard antibiotics (chloroamphenicol and terbinafin). The single crystal X-ray diffraction analysis of 1,3-dithia-2-stibacyclopentane 2,3-butylenedithiophosphate revealed a monodentate mode of bonding of the dithiophosphate ligand in the complex.Figure optionsDownload full-size imageDownload as PowerPoint slide