Related Experiment Video
Updated: Jun 11, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Tris(4-bromophenyl)aminium hexachloridoantimonate ('Magic Blue'): a strong oxidant with low inner-sphere
Mauricio Quiroz-Guzman1, Seth N Brown
1Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
Abstract:
Both the radical cation tris(4-bromophenyl)aminium hexachloridoantimonate ('Magic Blue'), (C(18)H(12)Br(3)N)[SbCl(6)], (I), and neutral tris(4-bromophenyl)amine, C(18)H(12)Br(3)N, (II), show extremely similar three-bladed propeller structures with planar N atoms. Key geometric features, such as the C-N bond distances and the angles between the planes of the aryl groups and the central NC(3) plane, are identical within experimental uncertainty in the two structures. This contrasts with the significant structural changes observed on oxidation of more electron-rich triarylamines, where resonance contributes to the stabilization of the radical cation, and suggests that, in general, more strongly oxidizing triarylaminium cations will have lower inner-sphere reorganization energies than their lower-potential analogues.
Related Concept Videos
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution: Elimination–Addition
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
