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](-) salts and characterized by multinuclear NMR and vibrational spectroscopy, and their X-ray crystal structures.
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA. haiges@usc.edu.
Ralf
R
Haiges
Amanda F
AF
Baxter
Nadine R
NR
Goetz
Joachim A
JA
Axhausen
Theresa
T
Soltner
Andreas
A
Kornath
Karl O
KO
Christe