Chloro(dimethyl sulfide)gold(I)

Chloro(dimethyl sulfide)gold(I)
Identifiers
CAS Number	29892-37-3 ;
3D model (JSmol)	separate form: Interactive image; coordination form: Interactive image;
ChemSpider	4809153 ;
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 Key: YQALRAGCVWJXGB-UHFFFAOYSA-M ; 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). verify (what is ?) 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

^ P. G. Jones and J. Lautner (1988). "Chloro(dimethyl sulfide)gold(I)". Acta Crystallogr. C. 44 (12): 2089–2091. doi:10.1107/S0108270188009151.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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] 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.

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