Synthesis, Spectroscopic, Structural Characterization, and Antimicrobial Studies of 1,3-Dithia-2-arsacyclopentane Derivatives with Oxygen and Sulfur Donor Ligands

Chauhan, H. P. S.; Bhatiya, Sumit; Bakshi, Abhilasha; Makwana, K. S.

doi:10.1080/10426507.2010.505742

Cited by 7 publications

(1 citation statement)

References 17 publications

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“…The known dimeric antimony(III) dialkyldithiocarbamates are usually associated, in their crystal structures, via secondary interactions of either SbÁ Á ÁS or C-HÁ Á ÁS type, leading to the formation of supramolecular aggregation (Alcock, 1972;Haiduc & Edelmann, 1999;Liu & Tiekink, 2005). To ascertain the validity of the co-existence of such interactions in the absence of steric bulk, in continuation of our interest in sulfurcontaining ligands (Chauhan et al, 2005;Chauhan et al, 2011;Chauhan et al, 2013) of a similar nature, here we describe the isolation of the title compound and characterize as dimeric such crystal structures in which both SbÁ Á ÁS and C-HÁ Á ÁS interactions co-exist in the absence of hydrogen-bonding functionality on the R (methyl) group. Interestingly, the title compound has quite a different crystal system (triclinic, P "…”

Section: Introductionmentioning

confidence: 99%

Supramolecular associationviaSb...S and C—H...S interactions in dimerictris(N,N-dimethyldithiocarbamato-S,S′)antimony(III): an approach to overcome the concept of steric bulk on such interactions

Chauhan

Carpenter

2013

Acta Crystallogr B

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Tris(N,N-dimethyldithiocarbamato-S,S')antimony(III) has been isolated as a dimer in acetonitrile. Single-crystal X-ray analysis shows that the molecule possesses both Sb···S and C-H···S interactions, which results in a supramolecular association in the absence of hydrogen-bonding functionality on the R group. The co-existence in the title compound of such interactions is a unique character of known dimeric antimony(III) alkyl and/or aryl dithiocarbamate complexes. The literature reveals that the species where the alkyl and/or aryl dithiocarbamates carry the following groups: R = methyl (chloroform solvated), ethyl, n-propyl, pyrrolidine, morpholine, piperidine, azepane, benzyl, methylphenyl, are not capable of forming significant hydrogen-bonding interactions. However, either Sb···S or C-H···S intermolecular interactions dominate between two centrosymmetrically related molecules leading to a supramolecular aggregation. In the species where the R group carries hydrogen-bonding functionality, i.e. 2-hydroxylethyl, the C-H···S interactions are subverted by O-H···O hydrogen bonding. In addition, the title compound does not have steric hindrance or any hydrogen-bonding group but is stabilized with the co-existence of Sb···S and C-H···S interactions. Analysis of the secondary interactions of a series of analogues previously reported reveals that steric bulk is unnecessary for the mitigation of Sb···S interactions and for the establishment of C-H···S secondary bonding.

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Section: Introductionmentioning

confidence: 99%

Supramolecular associationviaSb...S and C—H...S interactions in dimerictris(N,N-dimethyldithiocarbamato-S,S′)antimony(III): an approach to overcome the concept of steric bulk on such interactions

Chauhan

Carpenter

2013

Acta Crystallogr B

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

Chauhan

Carpenter

Joshi

2014

Applied Organom Chemis

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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.

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Synthesis, structural investigation, antibacterial and DFT studies of complexes derived from a cholesteryl dithiophosphonate ligand with some thio-metallolane and thio-metallocane heterocycles of As(III) and Sb(III)

Sosa-García

López-Cardoso

Tlahuext

et al. 2019

Inorganica Chimica Acta

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Synthesis, Spectroscopic, Structural Characterization, and Antimicrobial Studies of 1,3-Dithia-2-arsacyclopentane Derivatives with Oxygen and Sulfur Donor Ligands

Cited by 7 publications

References 17 publications

Supramolecular associationviaSb...S and C—H...S interactions in dimerictris(N,N-dimethyldithiocarbamato-S,S′)antimony(III): an approach to overcome the concept of steric bulk on such interactions

Supramolecular associationviaSb...S and C—H...S interactions in dimerictris(N,N-dimethyldithiocarbamato-S,S′)antimony(III): an approach to overcome the concept of steric bulk on such interactions

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

Synthesis, structural investigation, antibacterial and DFT studies of complexes derived from a cholesteryl dithiophosphonate ligand with some thio-metallolane and thio-metallocane heterocycles of As(III) and Sb(III)

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