Chloro(dimethyl sulfide)gold(I)

Chloro(dimethyl sulfide)gold(I)

Identifiers
CAS Number	29892-37-3  Y
3D model (JSmol)	separate form: Interactive image coordination form: Interactive image
ChemSpider	4809153  N
ECHA InfoCard	100.156.209
PubChem CID	6100873
CompTox Dashboard (EPA)	DTXSID001029475
InChI InChI=1S/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 N Key: YQALRAGCVWJXGB-UHFFFAOYSA-M N InChI=1/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 Key: YQALRAGCVWJXGB-REWHXWOFAH
SMILES separate form:[Au]Cl.CSC coordination form:Cl[Au-][S+](C)C
Properties
Chemical formula	C2H6AuClS
Molar mass	294.55 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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). N  verify  (what is  YN ?) 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 atom. 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

A simple preparation starts from elemental gold in DMSO / conc HCl (1:2) where DMSO acts as an oxidant and the formed Me₂S as ligand. As a side product, HAuCl₄·2DMSO is formed. ^[5]

Reactions

In chloro(dimethyl sulfide)gold(I), the dimethyl sulfide ligand is easily displaced by other ligands: ^[6]

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

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

When exposed to light, heat, or 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.
5. Mueller, Thomas E.; Green, Jennifer C.; Mingos, D. Michael P.; McPartlin, Jennifer C.; Whittingham, Conrad; Williams, David J.; Woodroffe, Thomas M. (1998). "Complexes of gold(I) and platinum(II) with polyaromatic phosphine ligands". J. Organomet. Chem. 551 (1–2): 313. doi:10.1016/S0022-328X(97)00522-6.
6. de Orbe, M. Elena; Echavarren, Antonio M. (2016). "Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I)". Org. Synth. 93: 115. doi: 10.15227/orgsyn.093.0115 .