Chloro(dimethyl sulfide)gold(I)
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| verifiedrevid = 418401548
| ImageFile1 = Chloro(dimethyl_sulfide)gold(I).png
| ImageSize1 =
| ImageAlt1 = structural formula of the title molecule
| ImageFile2 = Chloro(dimethyl-sulfide)gold(I)-from-xtal-1988-CM-3D-shiny-balls.png
| ImageSize2 =
| ImageAlt2 = ball-and-stick model of the molecule derived from the crystal structure
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|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 29892-37-3
| PubChem = 6100873
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4809153
| SMILES = [Au]Cl.CSC
| SMILES_Comment = separate form
| SMILES1 = Cl[Au-][S+](C)C
| SMILES1_Comment = coordination form
| InChI = 1/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1
| InChIKey = YQALRAGCVWJXGB-REWHXWOFAH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YQALRAGCVWJXGB-UHFFFAOYSA-M}}
|Section2={{Chembox Properties
| Au=1 | C=2 | H=6 | Cl=1 | S=1
| MolarMass =
| Appearance =
| Density =
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|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| AutoignitionPt = }}
|Section4={{Chembox Related
| OtherCompounds = chloro(tetrahydrothiophene)gold(I)
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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.{{cite journal | journal = Acta Crystallogr. C | volume = 44 | issue = 12 | year = 1988 | pages = 2089–2091 | doi = 10.1107/S0108270188009151 | title = Chloro(dimethyl sulfide)gold(I) | author = P. G. Jones and J. Lautner| doi-access = free }}
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.{{cite journal | doi = 10.1039/b005251p | journal = J. Chem. Soc., Dalton Trans. | issue = 24 | year = 2000 | pages = 4601–4606 | title = Luminescent gold(I) macrocycles with diphosphine and 4,4-bipyridyl ligands | author = Marie-Claude Brandys , Michael C. Jennings and Richard J. Puddephatt}} Alternatively, sodium tetrachloroaurate may be used as the source of gold(III).{{cite journal | doi = 10.1055/s-2007-984501 | title = Gold-Catalyzed Intermolecular Hydroamination of Allenes: First Example of the Use of an Aliphatic Amine in Hydroamination | year = 2007 | last1 = Nishina | first1 = Naoko | last2 = Yamamoto | first2 = Yoshinori | journal = Synlett | volume = 2007 | issue = 11 | pages = 1767}} The bromo analog, Me2SAuBr, has also been synthesized by a similar route.{{cite journal | doi = 10.1021/ja804027j | title = 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 | pmid = 18729360 | year = 2008 | last1 = Hickey | first1 = James L. | last2 = Ruhayel | first2 = Rasha A. | last3 = Barnard | first3 = Peter J. | last4 = Baker | first4 = Murray V. | last5 = Berners-Price | first5 = Susan J. | last6 = Filipovska | first6 = Aleksandra | journal = J. Am. Chem. Soc. | volume = 130 | issue = 38 | pages = 12570–1}}
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.{{cite journal | doi = 10.1016/S0022-328X(97)00522-6 | title = Complexes of gold(I) and platinum(II) with polyaromatic phosphine ligands | year = 1998 | last1 = Mueller | first1 = Thomas E. | last2 = Green | first2 = Jennifer C. | last3 = Mingos | first3 = D. Michael P. | last4 = McPartlin | first4 = Jennifer C.| last5 = Whittingham | first5 = Conrad | last6 = Williams | first6 = David J. | last7 = Woodroffe | first7 = Thomas M. | journal = J. Organomet. Chem. | volume = 551 | issue = 1–2 | pages = 313}}
Reactions
In chloro(dimethyl sulfide)gold(I), the dimethyl sulfide ligand is easily displaced by other ligands:{{cite journal| title=Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I) |first1=M. Elena|last1=de Orbe|first2=Antonio M.|last2=Echavarren|journal=Org. Synth.|year=2016|volume=93|page=115|
doi=10.15227/orgsyn.093.0115|doi-access=free}}
: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.