Synthesis and characterization of antimony (III) heteroleptic derivatives having oxygen, nitrogen and sulfur containing organic moieties with their antibacterial and antioxidant activities

Abstract

Six antimony(III) heteroleptic derivatives of the type [(R)(R′)C = NO]₂$\mathrm{S}\mathrm{b}\left[{\mathrm{S}}_2\mathrm{C}\stackrel{︹}{\mathrm{N}\mathrm{C}{\mathrm{H}}_2{(\mathrm{C}{\mathrm{H}}_2)}_3\mathrm{C}}{\mathrm{H}}_2\right]$[where R= –C₆H₅, R′= –CH₃ (A); R= –C₆H₄CH₃, R′= –CH₃ (B); R= –C₆H₄Cl, R′= –CH₃ (C); R= –C₆H₄Br, R′= –CH₃ (D); R= –C₆H₄OH, R′= –H (E); R(R′)C = $\stackrel{︹}{\mathrm{C}–\mathrm{C}{\mathrm{H}}_2–{(\mathrm{C}{\mathrm{H}}_2)}_3–\mathrm{C}}{\mathrm{H}}_2$ (F)] have been synthesized by the reactions of antimony trichloride with the sodium salt of substituted oximes and piperidine dithiocarbamate in 1:2:1 stoichiometry. These heteroleptic derivatives have been characterized by physico-chemical and elemental analyses (C, H, N, S and Sb). The tentative structures have been proposed on the basis of IR, ¹H and ¹³C NMR spectral and LC-mass spectrometry. The oxime moiety behaves as a unidentate ligand whereas the dithiocarbamate moiety behaves in mono functional anisobidentate manner. Distorted trigonal bipyramidal geometry around antimony metal has been proposed for these derivatives. Powder XRD study revealed that derivative (A) has nano range particle size, which supports the crystalline nature of the derivative. These newly synthesized heteroleptic antimony(III) derivatives have been examined against the B. Subtilis (gram positive) and E. coli (gram negative) bacteria for antibacterial potential and two derivatives [(C₆H₅)(CH₃)C = NO]₂Sb[S₂C$\stackrel{︹}{\mathrm{N}\mathrm{C}{\mathrm{H}}_2{(\mathrm{C}{\mathrm{H}}_2)}_3\mathrm{C}{\mathrm{H}}_2}$] (A) and [(C₆H₄CH₃)(CH₃)C = NO]₂Sb[S₂C $\stackrel{︹}{\mathrm{N}\mathrm{C}{\mathrm{H}}_2{(\mathrm{C}{\mathrm{H}}_2)}_3\mathrm{C}{\mathrm{H}}_2}$] (B) were examined for their antioxidant activity. Structural-activity relationship for antibacterial potential amongst the six derivatives (A-F) was also explored.

Graphical Abstract

Keywords:

• Substituted oximes
• dithiocarbamate
• trigonal bipyramidal geometry
• antibacterial and antioxidant

Acknowledgement

The work was supported by the Zoology Department, University of Rajasthan, Jaipur 30200, India and the Seminal applied Sciences Pvt. Ltd, B-33 Lal Kothi behind Sahara chambers Rajasthan, Jaipur-302017, India. Elemental analyses as well as Spectral studies were carried out at The Sophisticated Analytical Instrument Facility (SAIF) of Punjab University, Chandigarh. The powder X-ray diffraction was carried out from MNIT, Jaipur.