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Chloro(dimethyl sulfide)gold(I)

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Chloro(dimethyl sulfide)gold(I)
structural formula of the title molecule
ball-and-stick model of the molecule derived from the crystal structure
Identifiers
CAS Number
ECHA InfoCard 100.156.209 Edit this at Wikidata
CompTox Dashboard (EPA)
Properties
Chemical formula C2H6AuClS
Molar mass 294.55 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Chloro(dimethyl sulfide)gold(I) is an coordination complex of gold. It is a white solid. This compound is a common entry point into gold chemistry.

Structure

As for many other gold(I) complexes, the compound adopts a nearly linear (176.9°) geometry about the central gold centre. The Au-S bond distance is 2.271(2) Å, which is similar to other gold(I)-sulfur bonds.

Preparation

Chloro(dimethyl sulfide)gold(I) is commercially available. It may be prepared by dissolving gold in aqua regia (to give chloroauric acid), followed by addition of dimethyl sulfide. Alternatively, sodium tetrachloroaurate may be used as the source of gold(III). The bromo analog, Me2SAuBr, has also been synthesized by a similar route. An approximate equation is:

HAuCl4 + 2 SMe2 + H2O → Me2SAuCl + 3 HCl + OSMe2

Reactions

In chloro(dimethyl sulfide)gold(I), the dimethyl sulfide ligand is easily displaced by other ligands:

Me2SAuCl + L → LAuCl + Me2S (L = ligand)

Since Me2S is volatile, the new complex LAuCl is often easily purified.

When exposed to light and air, the compound decomposes to elemental gold.

References

  1. P. G. Jones and J. Lautner (1988). "Chloro(dimethyl sulfide)gold(I)". Acta Cryst. C. 44 (12): 2089–2091. doi:10.1107/S0108270188009151.
  2. Marie-Claude Brandys , Michael C. Jennings and Richard J. Puddephatt (2000). "Luminescent gold(I) macrocycles with diphosphine and 4,4-bipyridyl ligands". J. Chem. Soc., Dalton Trans. (24): 4601–4606. doi:10.1039/b005251p.
  3. Nishina, Naoko; Yamamoto, Yoshinori (2007). "Gold-Catalyzed Intermolecular Hydroamination of Allenes: First Example of the Use of an Aliphatic Amine in Hydroamination". Synlett. 2007 (11): 1767. doi:10.1055/s-2007-984501.
  4. Hickey, James L.; Ruhayel, Rasha A.; Barnard, Peter J.; Baker, Murray V.; Berners-Price, Susan J.; Filipovska, Aleksandra (2008). "Mitochondria-Targeted Chemotherapeutics: The Rational Design of Gold(I)N-Heterocyclic Carbene Complexes That Are Selectively Toxic to Cancer Cells and Target Protein Selenols in Preference to Thiols". J. Am. Chem. Soc. 130 (38): 12570. doi:10.1021/ja804027j. PMID 18729360.
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