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Tris(4-bromophenyl)ammoniumyl hexachloroantimonate
Identifiers
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 -BrC6 H4 )3 N•]+ [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).
Chemical compound
Tris(4-bromophenyl)ammoniumyl hexachloroantimonate is the
organic compound with the formula [(4-BrC6 H4 )3 N]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 SbCl− 6 , which is octahedral.
[3]
Related compounds
Magic green, tris(2,4-dibromophenyl)ammoniumyl hexachloroantimonate,
[4]
References
^ 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 .
^ 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 .
^
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 )
^ 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 .