Influence of structure on N–NO bond cleavage of aliphatic N-nitrosamines

N-Nitrosamines can be considered as potential NO/NO+ donors. Previous studies demonstrated that aromatic N-nitrosoureas and aromatic N-nitrosamines can act as donors of NO. The relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release and capture of NO or its redox forms remains unclear. In this paper we show that aliphatic N-nitrosamines of 7-azabicyclo[2.2.1]heptanes can undergo N–NO bond cleavage, and we also postulate that N-nitrosamines which enhance N–NO bond cleavage have low rotational barriers with respect to the N–NO bonds.