Chloro(dimethyl sulfide)gold(I)

Chloro(dimethyl sulfide)gold(I)

Identifiers
CAS Number	29892-37-3
ChemSpider	4809153
Jmol interactive 3D	Image
PubChem	6100873
InChI InChI=1S/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 Key: YQALRAGCVWJXGB-UHFFFAOYSA-M InChI=1/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 Key: YQALRAGCVWJXGB-REWHXWOFAH
SMILES [Au]Cl.S(C)C
Properties
Chemical formula	C2H6AuClS
Molar mass	294.55 g·mol^−1
Hazards
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26-S36
Related compounds
Related compounds	chloro(tetrahydrothiophene)gold(I)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chloro(dimethyl sulfide)gold(I) is a 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.^[1]

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.^[2] Alternatively, sodium tetrachloroaurate may be used as the source of gold(III).^[3] The bromo analog, Me₂SAuBr, has also been synthesized by a similar route.^[4] 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 Crystallogr. 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): 12570–1. doi:10.1021/ja804027j. PMID 18729360.