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

Abstract

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.

Perplexing Coordination Behaviour of Potentially Bridging Bipyridyl-Type Ligands in the Coordination Chemistry of Zinc and Cadmium 1,1-Dithiolate Compounds

“…Supramolecular layers are also formed in the R = Et analogue, 48. The assembly is distinct, as in Figure 10b The propensity of such hydrogen bonds in -S 2 CNCH 2 CH 2 OH dithiocarbamate ligands has been summarised recently, a summary which suggested these are relatively common in the structural chemistry of these ligands [73]. bonding potential, a three-dimensional architecture ensues, Figure 10d.…”

“…dithiocarbamate ligands has been summarised recently, a summary which suggested these are relatively common in the structural chemistry of these ligands [73]. The next structure to be described was isolated from frustrated experiments to force the formation of a coordination polymer by having an excess of bpy in the crystallisation.…”

1-(2-Hydroxyethyl)imidazolidine-2-thione

“…Such cyclization reactions have been documented in dithiocarbamate chemistry as being a convenient method to form 1-alkyl-2-imidazolidinethiones [8,9], suggesting the organotin reagent is not required for the synthesis. The motivation for the original reaction was to generate bioactive organotin dithiocarbamate compounds inspired by their biological activity, primarily anti-cancer and anti-microbial [10], and as a result of the recent reports of the potential anti-cancer (gold [11], bismuth [12], and zinc [13]) and anti-microbial (copper, silver [14] and gold [15,16]) activities of metal hydroxyethyl-substituted dithiocarbamate compounds, the biological activity of metal dithiocarbamates has been reviewed [17]. Herein, the spectroscopic characterization and X-ray crystal structure determination of 1 are reported.…”

“…The thioamide-N-H … O(hydroxyl) and hydroxyl-O-H … S(thione) hydrogen bonds are shown as blue and orange dashed lines, respectively. Selected geometric parameters for the specified intermolecular interactions: N1-H1n … O1 i = 2.045(17) Å, N1 … O1 i = 2.8428(15) Å with angle at H1n = 163.8(14)°; O1-H1o … S1 ii = 2.324(19) Å, O1 … S1 ii = 3.1757(10) Å with angle at H1o = 168.2(19)°. Symmetry operations: i 2 − x, −½ + y, ½ -z and ii x, ½ -y, −½ + z.…”

Crystal Chemistry of Zinc, Cadmium and Mercury

“…S hydrogen bonds instead. The propensity of such hydrogen bonds in -S 2 CNCH 2 CH 2 OH dithiocarbamate ligands has been summarised recently, a summary which suggested these are relatively common in the structural chemistry of these ligands[73].…”