Chloro(triphenylphosphine)gold(I)

Chemical compound From Wikipedia, the free encyclopedia

Chloro(triphenylphosphine)gold(I) or triphenylphosphinegold(I) chloride is a coordination complex with the formula (Ph3P)AuCl. This colorless solid is a common reagent for research on gold compounds.

Quick facts Identifiers, Properties ...
Chloro(triphenylphosphine)gold(I)
Skeletal formula of chloro(triphenylphosphine)gold(I)
Space-filling model of the chloro(triphenylphosphine)gold(I) molecule
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.636 Edit this at Wikidata
EC Number
  • 238-117-6
UNII
  • InChI=1S/C18H15P.Au.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h1-15H;;1H/q;+1;/p-1 ☒N[pubchem]
    Key: IFPWCRBNZXUWGC-UHFFFAOYSA-M ☒N
  • separate form: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Au]
  • coordination form: Cl[Au-][P+](c0ccccc0)(c0ccccc0)c0ccccc0
Properties
C18H15AuClP
Molar mass 494.71 g·mol−1
Appearance Colorless solid
Density 1.97 g/cm3
Melting point 236–237 °C (457–459 °F; 509–510 K)
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and structure

The complex is prepared by reducing chloroauric acid with triphenylphosphine in 95% ethanol:[1][2]

HAuCl4 + H2O + 2 PPh3 → (Ph3P)AuCl + Ph3PO + 3 HCl (Ph = phenyl, C6H5)

Chloro(triphenylphosphine)gold(I) can also be prepared by treating (dimethyl sulfide)gold(I) chloride (((CH3)2S)AuCl) with triphenylphosphine.[3]

The complex adopts a linear coordination geometry, which is typical of most gold(I) compounds.[4] It crystallizes in the orthorhombic space group P212121 with a = 12.300(4) Å, b = 13.084(4) Å, c = 10.170(3) Å with Z = 4 formula units per unit cell.[5]

Reactivity

Triphenylphosphinegold(I) chloride is a precursor to gold(I) catalyst used in organic synthesis.[3] Typically, it is treated with silver(I) salts of weakly coordinating anions (e.g., X– = SbF6–, BF4–, TfO–, or Tf2N–) to generate a weakly bound Ph3PAu–X complex. Among these, only the bistriflimide complex Ph3PAuNTf2 can be purified.[6] The nitrate complex Ph3PAuONO2 and the oxonium species [(Ph3PAu)3O]+[BF4]– are also prepared from the chloride.[7]

Triphenylphosphinegold(I) chloride is an entry reagent for organogold chemistry. The methyl complex Ph3PAuMe is prepared from triphenylphosphinegold(I) chloride by transmetalation with a Grignard reagent. Further treatment of Ph3PAuMe with methyllithium displaces the phosphine ligand and generates lithium dimethylaurate.[8][9]

Methylation of triphenylphosphinegold(I) chloride.

References

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