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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
3D model ( JSmol)
ChemSpider
ECHA InfoCard 100.156.209 Edit this at Wikidata
PubChem CID
  • 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
  • separate form: [Au]Cl.CSC
  • coordination form: Cl[Au-][S+](C)C
Properties
C2H6AuClS
Molar mass 294.55 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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 checkY☒N ?)

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.
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