Doi: 10.1016/j.cplett.2004.09.127
The enormous apparent gas-phase acidity of cubylamine
The high acidity of cubylamine (1NH2) seems to originate in the release of strain energy attending the breaking of some C–C bonds in 1NH−. This process is greatly facilitated by the strong stereoelectronic interactions in 1NH−. The anionic species thus formed are less strained, and their corresponding conjugate acids seem unable to ‘borrow strength’ from the residual strain, at least within the time-scale of the FT ICR experiments.