The influence of cation upon the supramolecular aggregation patterns of dithiocarbamate anions functionalised with hydrogen bonding capacity—the prevalence of charge-assisted O–H⋯S interactions

Howie, R. Α.; Lima, Geraldo Μ. de; Menezes, Daniele C.; Wardell, Jámes L.; Wardell, Solange M. S. V.; Young, David J.; Tiekink, Edward R. T.

doi:10.1039/b809730e

Cited by 52 publications

(27 citation statements)

References 40 publications

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“…Further, charge-assisted hydroxyl-O-H … S -(dithiocarbamate) hydrogen bonding features prominently in a series of salts of dithiocarbamate anions bearing hydroxylethyl substituents. [46]. The wide range of observed hydrogen bonding patterns in these structures perhaps provides an explanation why disorder in the hydroxyethyl residues is prevalent in these systems.…”

Section: Ch2cl2mentioning

confidence: 99%

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Jamaludin

Halim

Khoo

et al. 2016

Zeitschrift Für Kristallographie - Crystalline Materials

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Keywords: Copper(I) / silver(I) / dithiocarbamate / crystal structure analysis / X-ray diffraction Abstract.The crystal and molecular structures of (Ph3P)2M[S2CN(Me)CH2CH2OH], M = Cu, isolated as a 1:1 dichloromethane solvate (1.CH2Cl2), and M = Ag (4) show the central metal atom to be coordinated by a symmetrically (1.CH2Cl2) and asymmetrically chelating (4) dithiocarbamate ligand. The distorted tetrahedral geometries are completed by two PPh3 ligands. The presence of hydroxyl-O-H … S(dithiocarbamate) hydrogen bonds leads to centrosymmetric dimeric aggregates in each crystal structure. In the molecular packing of 1.CH2Cl2, channels comprising 1 are formed via aryl-C-H … O interactions with the solvent molecules associated with the walls of the channels via methylene-C-H … S, π(aryl) interactions. For 4, the dimeric aggregates are connected via a network of aryl-C-H … π(aryl) interactions. Preliminary screening for antimicrobial activity was conducted. The compounds were only potent against Gram-positive bacteria. Some further selectivity in activity was noted. Most notably, all compounds were active against methicillin resistant Staphylococcus aureus.

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Section: Ch2cl2mentioning

confidence: 99%

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Jamaludin

Halim

Khoo

et al. 2016

Zeitschrift Für Kristallographie - Crystalline Materials

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“…The R3PAuCl precursors were synthesized by reducing HAuCl4 (Sigma-Aldrich) with sodium sulfite followed by addition of the respective phosphane ligand, i.e., Ph3P (Merck), Cy3P (Acros), and Et3P (Sigma-Aldrich). The dithiocarbamate salts were prepared in quantitative yields from the reaction of the respective amine with KOH or NaOH and CS2, following literature precedents [45] …”

Section: Methodsmentioning

confidence: 99%

In vitro antibacterial and time kill evaluation of mononuclear phosphanegold(I) dithiocarbamates

Chen

Jamaludin

Khoo

et al. 2016

Journal of Inorganic Biochemistry

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Four compounds, R3PAu[S2CN(CH2CH2OH)2], R = Ph (1) and Cy (2), and Et3PAuS2CNRꞌ2, Rꞌ = Rꞌ = Et (3) and Rꞌ2 = (CH2)4 (4), have been evaluated for antibacterial activity against a panel of 24 Gram positive (8) and Gram negative (16) bacteria. Based on minimum inhibitory concentration (MIC) scores, compounds 1 and 2 were shown to be specifically potent against Gram positive bacteria whereas compounds 3 and, to a lesser extent, 4 exhibited broad range activity.All four compounds were active against methicillin resistant Staphylococcus aureus (MRSA).Time kill assays revealed the compounds to exhibit both time-and concentration-dependent pharmacokinetics against susceptible bacteria. Each compound was bactericidal against one or more bacteria with 3 being especially potent after 8 h exposure; compounds 1 and 3 were bactericidal against MRSA. Compound 3 was the most effective bactericide across the series especially toward B. subtilis, S. saprophyticus, A. hydrophilia, P. vulgaris, and V. parahaemolyticus. This study demonstrates the potential of this class of compounds as antibacterial agents, either broad range or against specific bacteria.

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“…The symmetry takes the form of a mirror plane perpendicular to the plane of the ring and passing through S(4), C(4) and the mid-point of the S(1)AS (2) bond. The point of attachment of the disulfide link between the dithiole rings means that the negative charges in the dianion are sustained by 1,3-dithiolate groups as opposed to the more usual 1,1-configuration as found, for example, in dithiocarbamates [23,24]. The dithiole rings and the substituent sulfur atoms are essentially planar entities with no greater displacement from the l.s.q.…”

Section: Resultsmentioning

confidence: 97%

Synthesis, characterization and crystal structure of dicesium bis(1,2-dithiole-3,5-dithiolato-4-yl)disulfide

Bordinhão

Comerlato

Cortas

et al. 2010

Inorganica Chimica Acta

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The influence of cation upon the supramolecular aggregation patterns of dithiocarbamate anions functionalised with hydrogen bonding capacity—the prevalence of charge-assisted O–H⋯S interactions

Cited by 52 publications

References 40 publications

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay

In vitro antibacterial and time kill evaluation of mononuclear phosphanegold(I) dithiocarbamates

Synthesis, characterization and crystal structure of dicesium bis(1,2-dithiole-3,5-dithiolato-4-yl)disulfide

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