Wikipedia

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate

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]

Tris(4-bromophenyl)ammoniumyl hexachloroantimonate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=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
    Key: SDHBPVANTRLAKE-UHFFFAOYSA-H
  • 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
Properties
[(p-BrC6H4)3N•]+[SbCl6]−
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).

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 SbCl−
6, which is octahedral.[3]

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

References

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  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 978-0-471-93623-7.
  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. Bibcode:2010AcCrC..66M.171Q. doi:10.1107/S0108270110019748. PMID 20603548.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
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