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Chloro(dimethyl sulfide)gold(I)

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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
  • 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[edit]

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[edit]

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[edit]

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[edit]

  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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