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⚫ | Section2 = {{Chembox Properties
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⚫ | Au = 1 | C = 2 | H = 6 | Cl = 1 | S = 1
| SMILES = Cl.CSC
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| SMILES_Comment = separate form
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| SMILES1 = Cl(C)C
⚫ | Density =
| SMILES1_Comment = coordination form
⚫ | MeltingPt =
| 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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⚫ | Au=1 | C=2 | H=6 | Cl=1 | S=1
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⚫ | Density =
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⚫ |Section3={{Chembox Hazards
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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. '''Chloro(dimethyl sulfide)gold(I)''' is a ] of ]. It is a white solid. This compound is a common entry point into gold chemistry.


==Structure== ==Structure==
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> 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>


==Preparation== ==Preparation==
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> 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>
An approximate equation is: An approximate equation is:
:HAuCl<sub>4</sub> + 2 SMe<sub>2</sub> + H<sub>2</sub>O &rarr; Me<sub>2</sub>SAuCl + 3 HCl + OSMe<sub>2</sub> :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>

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>


==Reactions== ==Reactions==
In chloro(dimethyl sulfide)gold(I), the ] ligand is easily displaced by other ligands: 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|
doi=10.15227/orgsyn.093.0115|doi-access=free}}</ref>
:Me<sub>2</sub>SAuCl + L &rarr; LAuCl + Me<sub>2</sub>S (L = ligand) :Me<sub>2</sub>SAuCl + L → LAuCl + Me<sub>2</sub>S (L = ligand)
Since Me<sub>2</sub>S is volatile, the new complex LAuCl is often easily purified. Since Me<sub>2</sub>S is volatile, the new complex LAuCl is often easily purified.


When exposed to light and air, the compound decomposes to elemental gold. When exposed to light, heat, or air, the compound decomposes to elemental gold.


==References== ==References==
{{reflist}} {{reflist}}
{{Gold compounds}}


] ]
⚫ ]
] ]
⚫ ]
]
]

Latest revision as of 12:38, 9 February 2024

Chloro(dimethyl sulfide)gold(I)
structural formula of the title molecule
ball-and-stick model of the molecule derived from the crystal structure
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.209 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1Key: YQALRAGCVWJXGB-UHFFFAOYSA-M
  • InChI=1/C2H6S.Au.ClH/c1-3-2;;/h1-2H3;;1H/q;+1;/p-1Key: YQALRAGCVWJXGB-REWHXWOFAH
SMILES
  • separate form: Cl.CSC
  • coordination form: Cl(C)C
Properties
Chemical formula C2H6AuClS
Molar mass 294.55 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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. Alternatively, sodium tetrachloroaurate may be used as the source of gold(III). The bromo analog, Me2SAuBr, has also been synthesized by a similar route. 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.

Reactions

In chloro(dimethyl sulfide)gold(I), the dimethyl sulfide ligand is easily displaced by other ligands:

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.
Gold compounds
Gold(-I)
Gold(I)
Organogold(I) compounds
  • (AuC6H2(CH3)3)5
  • (C2H5)3PAuSC5H5O(CO2CH3)3CH2OCOCH3
  • AuSC5H5O(OH)3CH2OH
  • NaAuSCH2CHOHCH2SO3
  • BrAuSC4H8
  • ClAuSC4H8
  • ClAuS(CH3)2
  • ClAuP(C6H5)3
  • Na2AuSCHCO2CH2CO2
  • NaAuSCHCO2CH2CO2H
    • Gold(II)
    Gold(I,III)
    Gold(III)
    Aurates(III)
  • HAuCl4
  • NaAuCl4
  • HAuBr4
  • HAu(NO3)4
  • ClO2Au(ClO4)4
  • NaAuO2
    • Gold(V)
    Gold(VI)
    Categories: