Portal de Periódicos da CAPES

The gas-phase anionic chemistry of saturated and unsaturated aliphatic nitriles

1980; Elsevier BV; Volume: 33; Issue: 1 Linguagem: Inglês

10.1016/0020-7381(80)80030-1

1873-3034

John H. Dawson, N. M. M. Nibbering,

Organic and Inorganic Chemical Reactions

The gas-phase ion—molecule chemistry of anions derived from some small saturated and unsaturated nitriles has been investigated using an ion cyclotron resonance mass spectrometer. O−. generated from nitrous oxide was employed as the principal primary reactantion. It has been found, inter alia, that conjugated unsaturated nitriles exhibit behaviour characteristic of a Michael addition reaction. Ions derived from nitriles have been allowed to interact with reagents such as aldehydes, methyl formate, carbonyl fluoride and tetrafluoroethylene. Three experimental results are described, which show that the isomeric ions fx CN and fx CN are distinct stable species, in the gas phase as in solution. It is reported that cyclopropanecarboxynitrile undergoes a reaction with O−. in which H2+ is abstracted from one corner of the ring, and the question of the long term structure of this and other stable (M  H2)−. ions is discussed.