Anomeric effect in N-azidomethylpyrrolidine: gas-phase electron diffraction and theoretical study

作者:Dorofeeva Olga V*; Mitin Alexander V; Altova Ekaterina P; Karasev Nikolai M; Nabiev Orudzh G; Vilkov Lev V; Oberhammer Heinz
来源:Physical Chemistry Chemical Physics, 2011, 13(4): 1490-1498.
DOI:10.1039/c0cp00894j

摘要

Gas-phase electron-diffraction data and high-level quantum chemical calculations have been used to study the conformational behaviour of N-azidomethylpyrrolidine. The two most stable conformers with a relative abundance of about 80% at 298 K possess gauche orientation of the azidomethyl group around the C-N-pyr bond (C-N-azido gauche with respect to the endocyclic N-pyr-C bond). This orientation is a strong manifestation of an anomeric effect. The influence of the anomeric effect is also reflected in shortening of the C-N-pyr bond and lengthening of the C-N-azido bond as compared to such bonds in other compounds.

  • 出版日期2011