Chemistry:Tris(4-bromophenyl)ammoniumyl hexachloroantimonate

From HandWiki
Tris(4-bromophenyl)ammoniumyl hexachloroantimonate
MagicBlueStructureBr3.png
Identifiers
3D model (JSmol)
ChemSpider
Properties
[(p-BrC
6
H
4
)
3
N•]+
[SbCl
6
]
Molar mass 816.47 g·mol−1
Appearance blue solid
Melting point 141 to 142 °C (286 to 288 °F; 414 to 415 K)
acetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate is the organic compound with the formula [(4-BrC6H4)3N]SbCl6.[1] 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).[2]

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 SbCl6, which is octahedral.[3]

Related compounds

  • Magic green, tris(2,4-dibromophenyl)ammoniumyl hexachloroantimonate,[4]

References

  1. Earle, Martyn J.; Vibert, Aude; Jahn, Ullrich (2011). "Tris(4-bromophenyl)aminium Hexachloroantimonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt397.pub2. ISBN 978-0471936237. 
  2. Connelly, N. G.; Geiger, W. E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chem. Rev. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774. 
  3. Quiroz-Guzman, Mauricio; Brown, Seth N. (2010). "Tris(4-bromophenyl)aminium hexachloridoantimonate ('Magic Blue'): A strong oxidant with low inner-sphere reorganization". Acta Crystallographica Section C 66 (7): m171–m173. doi:10.1107/S0108270110019748. PMID 20603548. 
  4. Schmidt, Werner; Steckhan, Eberhard (1980). "Über organische Elektronenüberträgersysteme, I. Elektrochemische und spektroskopische Untersuchung bromsubstituierter Triarylamin‐Redoxsysteme". Chemische Berichte 113 (2): 577–585. doi:10.1002/cber.19801130215.