Mixed bis(morpholine‐4‐dithiocarbamato‐S,S′)antimony(III) complexes: synthesis, characterization and biological studies

Abstract

Some mixed bis(morpholine-4-dithiocarbamato-S,S′)antimony(III) complexes [(OC 4 H 8 NCS 2 ) 2 SbL] with oxygen or sulfur donor ligands [L = -OOCCH 3 (1), -OOCC 6 H 5 (2), -SOCCH 3 (3), -SCH 2 COOH (4), -OOCC 6 H 4 (OH) (5), -SCH 2 CH 2 CH 3 (6), -OC 6 H 5 (7), ½ -SCH 2 CH 2 S-(8)] have been synthesized by reacting the chloro-bis(morpholine-4-dithiocarbamato-S,S′)antimony(III) with corresponding oxygen or sulfur donor ligands in 1:1 or 2:1 stoichiometries. These have been characterized by melting point, molecular weight determination (cryoscopically), antimony (iodometrically) and sulfur (gravimetrically) estimation, elemental analyses (C, H and N), UV-visible, FT-IR, far IR, multinuclear NMR ( 1 H and 13 C)], TG/DTA analysis, ESI-mass and powder X-ray diffraction studies. The splitting of the strong band observed at 1046-1066 cm À1 due to υ(C-S) indicated anisobidentate mode of binding of the dithiocarbamate group, which was further supported by a 13 C NMR signal appearing at around δ 200 due to NCS 2 moiety. The base peak observed at m/z 444.9 supports the strong chelating nature of the morpholine-4-dithiocarbamate compared to the other hetero ligands used. TGA revealed that, complexes 21 and 4 were decomposed in three steps; also 6 was decomposed in two steps, followed by the formation of Sb 2 S 3 . The results obtained by antimicrobial screening tests indicate that complex 3 showed a maximum zone of inhibition (20 mm) against Trichoderma ressie at a concentration of 200 μg ml À1 . Complexes 2, 3 and 8 are most active (zone of inhibition (ZI) 17-20 mm) against both of the fungal species Aspergillus niger and Trichoderma ressie as well as complex 4 (ZI 17 mm) and 6 (ZI 18 mm) against Trichoderma ressie.

Lanthanide(iii) morpholine 4-dithiocarbamate complexes: Pr(iii) derivative shows first example of polymeric lanthanide(iii) dithiocarbamate

“…20 All complexes were characterized by conventional analytical and spectroscopic techniques. The solid state structures of 1-3 were determined by single crystal X-ray diffraction analyses.…”

“…Potassium salt of morpholine 4-dithiocarbamate has been prepared by the reaction of morpholine with carbon disulphide in presence of potassium hydroxide following the reported method. 20 Complexes [Ln(Phen)(Mph-Dtc) 3 ]$xCH 2 Cl 2 [Ln ¼ Pr (1), Nd (2) and Eu (3); Mph-Dtc ¼ morpholine 4-dithiocarbamate;…”

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

“…Overall, the compounds with L 55 showed better inhibition towards the bacterial strains tested (S. aureus, B. subtilis, E. coli, and P. aeruginosa) compared to those with L 56 . Chauhan et al also studied the antimicrobial properties of arsenic(III) and antimony(III) dithiocarbamates against four bacterial strains (S. aureus, B. subtilis, E. coli, and P. aeruguinosa) and two fungal species (A. niger and T. reesie) [108][109][110]. The investigated mono-nuclear compounds were [Sb(L 18,55 ) 2 ]X for X = O(O=)CMe, O(O=)CPh, O(S=)CMe, SCH 2 COOH, O(O=)CC 6 H 4 (OH), S(n-Pr), and OPh [109,110]; [M(L 18,55 ) 2 ] 2 X, for M(III) = As and Sb, X = -SCH 2 CH 2 S- [108,109], and M(L 55,56,65 ) 2 [S(S)P(Y) 2 ] for M(III) = As and Sb; Y = OPh and Ph [110].…”

Chemistry and Some Biological Potential of Bismuth and Antimony Dithiocarbamate Complexes

“…The obtained solids were all recrystallised in ethanol, dichloromethane, chloroform, and acetonitrile (or a mixture of these solvents). In the synthesis of mixed bis(morpholine-4-dithiocarbamato-S,S ) antimony(III) complexes, an intermediate compound of the Sb(III) dithiocarbamate complex was obtained [49]. This complex was synthesised by the reaction of a hexane solution of antimony(III) bromide with a hexane solution of potassium morpholine-4-dithiocarbamate ligand, and the product was obtained after refluxing for 5 h. Another report by Baba et al [50] involved the reaction of antimony(III) trichloride and Tris(N-cyclohexyl-N-methyl dithiocarbamato-S) ligands in ethanol (1/3 molar stoichiometry) [50].…”