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Revision as of 13:34, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475706317 of page Gold(III)_bromide for the Chem/Drugbox validation project (updated: 'CASNo').		Latest revision as of 21:06, 31 July 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,602 edits →Preparation: who knows what "drives" this reaction
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			{{Chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			| Verifiedfields = changed
	{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443849639
			| verifiedrevid = 477001840
	| ImageFile = Gold-tribromide-dimer-3D-balls.png		| ImageFile = Gold-tribromide-dimer-3D-balls.png
	| ImageSize = 200px
	| ImageName = Ball-and-stick model of gold(III) bromide		| ImageName = Ball-and-stick model of gold(III) bromide
	| ImageFile1 = Gold-tribromide-dimer-3D-vdW.png		| ImageFile1 = Gold-tribromide-dimer-3D-vdW.png
	| ImageSize1 = 200px
	| ImageName1 = Space-filling model of gold(III) bromide		| ImageName1 = Space-filling model of gold(III) bromide
	| IUPACName = Gold(III) bromide
	| OtherNames = Auric bromide<br />Gold bromide<br />Gold(III) bromide<br />Gold tribromide <br /> Digold hexabromide		| OtherNames = Auric bromide<br />Gold bromide<br />Gold(III) bromide<br />Gold tribromide <br /> Digold hexabromide
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| Abbreviations =		| Abbreviations =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 9548892		| ChemSpiderID = 9548892
			| EC_number = 233-654-2
			| Gmelin = 164245
	| InChI = 1S/Au.3BrH/h;3*1H/q+3;;;/p-3		| InChI = 1S/Au.3BrH/h;3*1H/q+3;;;/p-3
	| InChIKey = OVWPJGBVJCTEBJ-DFZHHIFOAK		| InChIKey = OVWPJGBVJCTEBJ-DFZHHIFOAK
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	| StdInChIKey = OVWPJGBVJCTEBJ-UHFFFAOYSA-K		| StdInChIKey = OVWPJGBVJCTEBJ-UHFFFAOYSA-K
	| InChIKey1 = OVWPJGBVJCTEBJ-UHFFFAOYSA-K		| InChIKey1 = OVWPJGBVJCTEBJ-UHFFFAOYSA-K
	| CASNo_Ref = {{cascite|correct|??}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = <!-- blanked - oldvalue: 10294-28-7 -->		| CASNo = 10294-28-7
			| UNII_Ref = {{fdacite|correct|FDA}}
	| CASOther = 11092-53-8
	| EINECS =		| UNII = 4PJV3VH75Y
	| PubChem = 82525		| PubChem = 82525
	| SMILES = ...		| SMILES = ...
			| SMILES_Comment = ionic form
	| InChI =
			| SMILES1 = Br1(Br)(1)(Br)Br <!-- 1()(1)() and Br1(Br)(1)(Br)Br have the right structure, but in those SMILES, the gold isn't in the +III oxidation state. -->
			| SMILES1_Comment = covalent form
	| RTECS =		| RTECS =
	| MeSHName =		| MeSHName =
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG =		| KEGG =
			}}
	| ATCCode_prefix =
			|Section2={{Chembox Properties
	| ATCCode_suffix =
			| Formula = {{chem2|AuBr3}}
	| ATC_Supplemental =}}
			| Au=1|Br=3
	| Section2 = {{Chembox Properties
			| Appearance = dark red to black crystals
	| Formula = AuBr<sub>3</sub>
	| MolarMass = 436.69 g/mol
	| Appearance = dark red to black crystalline
	| Density =		| Density =
	| MeltingPt = 97.5 °C		| MeltingPtC = 97.5
			| MeltingPt_notes =
	| Melting_notes =
	| BoilingPt =		| BoilingPt =
	| Boiling_notes =		| BoilingPt_notes =
			| Solubility = Slightly soluble<ref name="sigma aubromide">{{cite web |title=Gold(III) bromide 99.999% trace metals |url=https://www.sigmaaldrich.com/catalog/product/aldrich/398470?lang=en&region=US |website=Sigma Aldrich |access-date=27 May 2021}}</ref>
	| Solubility =
	| SolubleOther =		| SolubleOther =
	| Solvent =		| Solvent =
	| pKa =		| pKa =
	| pKb = }}		| pKb =
			}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| EUClass =
	| EUIndex =
	| MainHazards =		| MainHazards =
	| NFPA-H = 3		| NFPA-H = 3
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
	| RPhrases =
	| SPhrases =
	| RSPhrases =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| ExploLimits =		| ExploLimits =
	| PEL = }}		| PEL =
			| GHS_ref=<ref>{{cite web |title=Gold tribromide |url=https://pubchem.ncbi.nlm.nih.gov/compound/82525#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
			| GHSPictograms = {{GHS05}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|314}}
			| PPhrases = {{P-phrases|260|264|280|301+330+331|302+361+354|304+340|305+354+338|316|321|363|405|501}}
			}}
	}}		}}
			'''Gold(III) bromide''' is a dark-red to black crystalline solid.<ref name="Macintyre">Macintyre, J. E. (ed.) ''Dictionary of Inorganic Compounds''; Chapman & Hall: London, 1992; vol. 1, pp. 121</ref><ref name="Greenwood">Greenwood, N.N.; Earnshaw, A. ''Chemistry of the Elements''; Butterworth-Heineman: Oxford,1997; pp. 1183-1185</ref><ref name="Cotton">Cotton, F.A.; Wilkinson, G.; Murillo, C.A.; Bochmann, M. ''Advanced Inorganic Chemistry''; John Wiley & Sons: New York, 1999; pp. 1101-1102</ref> It has the ] {{chem2|AuBr3}}, but exists as a ] with the ] {{chem2|Au2Br6}} in which two gold atoms are ] by two bromine atoms.<ref name="Greenwood"/><ref name="Cotton"/><ref name="Schulz">Schulz, A.; Hargittai, M. '']'' '''2001''', vol. 7, pp. 3657-3670</ref> It is commonly referred to as gold(III) bromide, gold tribromide, and rarely but traditionally auric bromide, and sometimes as digold hexabromide. The analogous copper or silver tribromides do not exist.<ref name="Schwerdtferger1">Schwerdtfeger, P. '']'' '''1989''', vol. 111, pp. 7261-7262</ref>
			==History==
			The first mention of any research or study of the gold halides dates back to the early-to-mid-19th century, and there are three primary researchers associated with the extensive investigation of this particular area of chemistry: Thomsen, Schottländer, and Krüss.<ref name="Lengefield">Lengefield, F. '']'' '''1901''', vol. 26, pp. 324</ref><ref name="Thomsen">Thomsen, J. '']'' '''1876''', vol. 13, pp. 337</ref><ref name="Schottlander">
			Schottländer, '']'', vol. 217, pp. 312</ref><ref name="Kruss">Krüss, G. '']'' '''1887''', vol. 20, pp. 2634</ref>
			==Structure==
			Gold(III) bromide adopts structures seen for the other gold(III) trihalide dimeric compounds, such as the ]. The gold centers exhibit ] coordination with bond angles of roughly 90 degrees.<ref name="Cotton"/><ref name="Schulz"/>
			Calculations indicate that in the hypothetical monomeric forms of the gold trihalides, the ] causes differences to arise in the structures of the gold halide complexes. For instance, gold(III) bromide contains one long and two short gold-bromine bonds whereas gold(III) chloride and gold(III) fluoride consist of two long and one short gold-halogen bonds.<ref name="Schulz"/> Moreover, gold tribromide does not exhibit the same coordination around the central gold atom as gold trichloride or gold trifluoride. In the latter complexes, the coordination exhibits a T-conformation, but in gold tribromide the coordination exists as more of a dynamic balance between a Y-conformation and a T-conformation. This coordination difference can be attributed to the Jahn-Teller effect but more so to the decrease in ] of the gold atoms with the bromine ligands compared to the π-back bonding found with fluorine and chlorine ligands. It is also this decrease in π-back bonding which explains why gold tribromide is less stable than its trifluoride and trichloride counterparts.<ref name="Schulz"/>
			:]
			==Preparation==
			The most common synthesis method of gold(III) bromide is heating gold and excess liquid ] at 140&nbsp;°C:<ref name="Macintyre"/>
			:{{chem2|2 Au + 3 Br2 → Au2Br6}}
			Alternatively, the halide-exchange reaction of ] with ] has also been proven successful in synthesizing gold(III) bromide:<ref name="Dell">
			Dell'Amico, D.B.; Calderazzo, F.; Morvillo, A.; Pelizzi, G; Robino, P. '']'' '''1991,''' pp. 3009-3016</ref>
			:{{chem2|Au2Cl6 + 6 HBr → 6 HCl + Au2Br6}}
			==Chemical properties==
			Gold(III) displays square planar coordination geometry.<ref name="Cotton"/>
			Gold(III) trihalides form a variety of four-coordinate adducts.<ref name="Greenwood"/> One example is the hydrate {{chem2|AuBr3*H2O}}. Another well known adduct is that with ].<ref>{{cite journal |journal=Org. Synth.|doi=10.15227/orgsyn.096.0150 |title=Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes |date=2019 |last1=Nottingham |first1=Chris |first2=Verity|last2=Barber|first3=Guy C.|last3=Lloyd-Jonesjournal=Organic Syntheses |volume=96 |pages=150–178 }}</ref> The tetrabromide is also known:
			:{{chem2|HBr + AuBr3 → H+-}}
			==Uses==
			===Catalytic chemistry===
			Gold(III) bromide catalyzes a variety of reactions. In one example, it catalyzes the ] of an enynal unit and ].<ref name="Asao">Asao, N.; Aikawa, H.; Yamamoto, Y. '']'' '''2004''', vol. 126, pp. 7458-7459</ref>
			:]
			Another catalytic use of gold tribromide is in the ] reaction of propargylic alcohols. In this reaction, the gold complex serves as an alcohol-activating agent to facilitate the substitution.<ref name="Georgy">Georgy, M.; Boucard, V.; Campagne, J.'' ]'' '''2005''', vol. 127, pp. 14180-14181</ref>
			:]
			===Ketamine detection===
			Gold(III) bromide can be used as a testing reagent for the presence of ].<ref name='Microgram'>{{cite web|url=https://www.justice.gov/dea/programs/forensicsci/microgram/journal_v4_num14/pg3.html |title=A New, Highly Specific Color Test for Ketamine |access-date=2012-01-26 |last=Sarwar |first=Mohammad |work=The Microgram |publisher=Drug Enforcement Administration |url-status=dead |archive-url=https://web.archive.org/web/20101017125149/http://www.justice.gov/dea/programs/forensicsci/microgram/journal_v4_num14/pg3.html |archive-date=2010-10-17 }}</ref>
			0.25% {{chem2|AuBr3}} 0.1M NaOH is prepared to give a brownish-yellow solution. Two drops of this are added to a spotting plate and a small amount of ketamine is added. The mixture gives a deep purple color within approximately one minute, which turns to a dark, blackish-purple color within approximately two minutes.
			], ], ], ], ], ], and ] all cause an instant colour change to purple, as do other compounds with phenol and hydroxyl groups.
			Nothing commonly found in conjunction with ketamine gave the same colour change in the same time.
			"The initial purple color may be due to the formation of a complex between the gold and the ketamine. The cause for the change of color from purple to dark blackish-purple is unknown; however, it may be due to a redox reaction that produces a small amount of ]."<ref name="Microgram"/>
			{{commons category|Gold tribromide|lcfirst=yes}}
			==References==
			{{Reflist}}
			{{Gold compounds}}
			{{Bromides}}
			{{DEFAULTSORT:Gold(Iii) Bromide}}
			]
			]
			]
			]
			]