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

Dalton Trans. 2016 May 28;45(20):8494-9. doi: 10.1039/c6dt01301e. Epub 2016 Apr 26.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.