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Latest revision as of 12:38, 9 February 2024 edit undoM97uzivatel (talk | contribs)Extended confirmed users6,573 edits →References: redundant category |
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| ImageFile1 = Chloro(dimethyl_sulfide)gold(I).png |
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| ImageFile1 = Chloro(dimethyl_sulfide)gold(I).png |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 29892-37-3 |
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| CASNo = 29892-37-3 |
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| PubChem = 6100873 |
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| ChemSpiderID = 4809153 |
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| Au = 1 | C = 2 | H = 6 | Cl = 1 | S = 1 |
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| SMILES = Cl.CSC |
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| SMILES_Comment = separate form |
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| SMILES1 = Cl(C)C |
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| SMILES1_Comment = coordination form |
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| InChI = 1/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 |
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| InChIKey = YQALRAGCVWJXGB-REWHXWOFAH |
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| StdInChI = 1S/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1 |
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| StdInChIKey = YQALRAGCVWJXGB-UHFFFAOYSA-M}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| 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}} |
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'''Chloro(dimethyl sulfide)gold(I)''' is an ] of ]. It is a white solid. This compound is a common entry point into gold chemistry. |
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'''Chloro(dimethyl sulfide)gold(I)''' is a ] of ]. It is a white solid. This compound is a common entry point into gold chemistry. |
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==Structure== |
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==Structure== |
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As for many other gold(I) complexes, the compound adopts a nearly linear (176.9°) geometry about the central gold centre. The Au-S bond distance is 2.271(2) Å, which is similar to other gold(I)-sulfur bonds.<ref>{{cite journal | journal = ] 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}}</ref> |
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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.<ref>{{cite journal | journal = ] | 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 }}</ref> |
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==Preparation== |
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==Preparation== |
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Chloro(dimethyl sulfide)gold(I) is commercially available. It may be prepared by dissolving gold in ] (to give ]), followed by addition of ].<ref>{{cite journal | doi = 10.1039/b005251p | journal = ] | 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}}</ref> Alternatively, ] may be used as the source of gold(III).<ref>{{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 = ] | volume = 2007 | issue = 11 | pages = 1767}}</ref> The bromo analog, Me<sub>2</sub>SAuBr, has also been synthesized by a similar route.<ref>{{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 = ] | volume = 130 | issue = 38 | pages = 12570}}</ref> |
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Chloro(dimethyl sulfide)gold(I) is commercially available. It may be prepared by dissolving gold in ] (to give ]), followed by addition of ].<ref>{{cite journal | doi = 10.1039/b005251p | journal = ] | 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}}</ref> Alternatively, ] may be used as the source of gold(III).<ref>{{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 = ] | volume = 2007 | issue = 11 | pages = 1767}}</ref> The bromo analog, Me<sub>2</sub>SAuBr, has also been synthesized by a similar route.<ref>{{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 = ] | volume = 130 | issue = 38 | pages = 12570–1}}</ref> |
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An approximate equation is: |
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An approximate equation is: |
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:HAuCl<sub>4</sub> + 2 SMe<sub>2</sub> + H<sub>2</sub>O → Me<sub>2</sub>SAuCl + 3 HCl + OSMe<sub>2</sub> |
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:HAuCl<sub>4</sub> + 2 SMe<sub>2</sub> + H<sub>2</sub>O → Me<sub>2</sub>SAuCl + 3 HCl + OSMe<sub>2</sub> |
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A simple preparation starts from elemental gold in DMSO / conc HCl (1:2) where DMSO acts as an oxidant and the formed Me<sub>2</sub>S as ligand. As a side product, HAuCl<sub>4</sub>·2DMSO is formed.<ref>{{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 = ] | volume = 551 | issue = 1–2 | pages = 313}}</ref> |
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==Reactions== |
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==Reactions== |
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In chloro(dimethyl sulfide)gold(I), the ] ligand is easily displaced by other ligands: |
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In chloro(dimethyl sulfide)gold(I), the ] ligand is easily displaced by other ligands:<ref>{{cite journal| title=Intermolecular 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| |
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doi=10.15227/orgsyn.093.0115|doi-access=free}}</ref> |
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:Me<sub>2</sub>SAuCl + L → LAuCl + Me<sub>2</sub>S (L = ligand) |
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:Me<sub>2</sub>SAuCl + L → LAuCl + Me<sub>2</sub>S (L = ligand) |
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Since Me<sub>2</sub>S is volatile, the new complex LAuCl is often easily purified. |
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Since Me<sub>2</sub>S is volatile, the new complex LAuCl is often easily purified. |
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When exposed to light and air, the compound decomposes to elemental gold. |
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When exposed to light, heat, or air, the compound decomposes to elemental gold. |
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==References== |
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==References== |
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{{reflist}} |
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{{Gold compounds}} |
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