C-H Bond Dissociation Energies of Alkyl Amines: Radical Structures and Stabilization Energies

摘要

In the five-membered pyrrolidine ring the radical adopts an envelope conformation with the C~5 carbon atom at the vertex. This accommodates the favorable alignment of the sp orbitals of C and N but has no C-H eclipsing interactions like those which occur in the parent. Thus, in effect, there is a reduction of strain on formation of the radical, and the BDE is lowered by 8 kJ mol~-1 below that of typical secondary amines.