Chemistry:Chloro(dimethyl sulfide)gold(I)
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C2H6AuClS | |
| Molar mass | 294.55 g·mol−1 |
| Hazards | |
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
| Related compounds | |
Related compounds
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chloro(tetrahydrothiophene)gold(I) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| 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.
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