Chem. Phys. Lett. 398, 560-563 (2004)

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.