tris(4-bromophenyl)ammoniumyl hexachloroantimonate
{{Chembox
| ImageFile = File:MagicBlueStructureBr3.png
| ImageClass = skin-invert-image
| ImageSize =
| ImageAlt =
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo1 = 24964-91-8
| CASNo1_Comment = salt
| CASNo2 = 37881-41-7
| CASNo2_Comment = cation
| PubChem = 16688313
| ChemSpiderID = 21493919
| StdInChI=1S/C18H12Br3N.6ClH.Sb/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18;;;;;;;/h1-12H;6*1H;/q+1;;;;;;;+5/p-6
| StdInChIKey = SDHBPVANTRLAKE-UHFFFAOYSA-H
| SMILES = C1=CC(=CC=C1[N+](C2=CC=C(C=C2)Br)C3=CC=C(C=C3)Br)Br.Cl[Sb-](Cl)(Cl)(Cl)(Cl)Cl
}}
|Section2={{Chembox Properties
| Formula = {{chem2|[(p\-BrC6H4)3N•]+[SbCl6]-}}
| C=18|H=12|N=1|Br=3|Cl=6|Sb=1
| Appearance = blue solid
| Density =
| MeltingPtC = 141 to 142
| BoilingPt =
| Solubility = acetonitrile}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Tris(4-bromophenyl)ammoniumyl hexachloroantimonate is the organic compound with the formula [(4-BrC6H4)3N]SbCl6.{{cite book|doi=10.1002/047084289X.rt397.pub2|isbn=978-0-471-93623-7|chapter=Tris(4-bromophenyl)aminium Hexachloroantimonate|title=Encyclopedia of Reagents for Organic Synthesis|year=2011|last1=Earle|first1=Martyn J.|last2=Vibert|first2=Aude|last3=Jahn|first3=Ullrich}} Commonly known as magic blue, it is the hexachloroantimonate salt of an amine radical cation. It is a blue solid that reacts with many solvents but is soluble in acetonitrile. The compound is a popular oxidizing agent in organic and organometallic chemistry, with a reduction potential of 0.67 V versus ferrocene/ferrocenium (acetonitrile solution) or 0.70 V versus ferrocene/ferrocenium (dichloromethane solution).{{cite journal|first1=N. G.|last1= Connelly|first2= W. E.|last2= Geiger| title=Chemical Redox Agents for Organometallic Chemistry|journal=Chem. Rev.|year= 1996| volume= 96|issue=2| pages= 877–910| doi=10.1021/cr940053x| pmid=11848774}}
The structure of the cation consists of a three-bladed propeller structure with a planar amine. It is nearly identical to the parent triphenylamine. The weakly coordinating anion is {{chem|SbCl|6|−}}, which is octahedral.
{{cite journal|author = Quiroz-Guzman, Mauricio; Brown, Seth N.|title=Tris(4-bromophenyl)aminium hexachloridoantimonate ('Magic Blue'): A strong oxidant with low inner-sphere reorganization|journal=Acta Crystallographica Section C|volume=66|issue=7|pages=m171–m173|doi=10.1107/S0108270110019748|year=2010|pmid=20603548|bibcode=2010AcCrC..66M.171Q }}
Related compounds
- Magic green, tris(2,4-dibromophenyl)ammoniumyl hexachloroantimonate,{{cite journal |doi=10.1002/cber.19801130215|title=Über organische Elektronenüberträgersysteme, I. Elektrochemische und spektroskopische Untersuchung bromsubstituierter Triarylamin-Redoxsysteme |year=1980 |last1=Schmidt |first1=Werner |last2=Steckhan |first2=Eberhard |journal=Chemische Berichte |volume=113 |issue=2 |pages=577–585 }}