Angew. Chem. Int. Ed. 42, 2281-2284 (2003)

Doi: 10.1002/anie.200350993

Stereoelectronic, Strain, and Medium Effects on the Protonation of Cubylamine, a Janus-like Base

The cubic structure of cubylamine (1NH2) is maintained on protonation in aqueous solution, but in the gas phase 1NH2 is irreversibly protonated on the carbon framework, leading to the formation of iminium ions through ring opening (see scheme).