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

Literature Information

Publication Date 2010-12-07
DOI 10.1039/C0CP00894J
Impact Factor 3.676
Authors

Olga V. Dorofeeva, Alexander V. Mitin, Ekaterina P. Altova, Nikolai M. Karasev, Orudzh G. Nabiev, Lev V. Vilkov, Heinz Oberhammer


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Abstract

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–Npyr bond (C–Nazidogauche with respect to the endocyclic Npyr–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–Npyr bond and lengthening of the C–Nazido bond as compared to such bonds in other compounds.

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