Protonation of nitriles: isolation and characterization of alkyl- and arylnitrilium ions

The reactions of acetonitrile, propionitrile, butyronitrile, N,N-dimethylaminoacetonitrile, benzonitrile, o-tolunitrile and 1,4-dicyanobenzene with HF/AsF5 or HF/SbF5 in anhydrous HF result in protonation of the nitrile. The obtained nitrilium ions were isolated as [AsF6](-), [SbF6](-) and [Sb2F11](...

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Published inDalton transactions : an international journal of inorganic chemistry Vol. 45; no. 20; pp. 8494 - 8499
Main Authors Haiges, Ralf, Baxter, Amanda F, Goetz, Nadine R, Axhausen, Joachim A, Soltner, Theresa, Kornath, Andreas, Christe, Karl O
Format Journal Article
LanguageEnglish
Published England 28.05.2016
Subjects
Acetonitrile
Benzonitrile
Crystal structure
Nitriles
Nuclear magnetic resonance
Protonation
Spectroscopy
X-rays
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Summary:The reactions of acetonitrile, propionitrile, butyronitrile, N,N-dimethylaminoacetonitrile, benzonitrile, o-tolunitrile and 1,4-dicyanobenzene with HF/AsF5 or HF/SbF5 in anhydrous HF result in protonation of the nitrile. The obtained nitrilium ions were isolated as [AsF6](-), [SbF6](-) and [Sb2F11](-) salts and characterized by multinuclear NMR and vibrational spectroscopy, and their X-ray crystal structures.
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ISSN:1477-9226
1477-9234
DOI:10.1039/c6dt01301e