title: Anomeric effect in N-azidomethylpyrrolidine: gas-phase electron diffraction and theoretical study.
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-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.
authors.affiliation: Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow 119991, Russia. dorofeeva@phys.chem.msu.ru
authors.forename: Olga V
authors.initials: OV
authors.lastname: Dorofeeva
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Mitin
authors.forename: Ekaterina P
authors.initials: EP
authors.lastname: Altova
authors.forename: Nikolai M
authors.initials: NM
authors.lastname: Karasev
authors.forename: Orudzh G
authors.initials: OG
authors.lastname: Nabiev
authors.forename: Lev V
authors.initials: LV
authors.lastname: Vilkov
authors.forename: Heinz
authors.initials: H
authors.lastname: Oberhammer