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

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

doi:10.1039/C0CP00894J

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

Olga V. Dorofeeva,*^a Alexander V. Mitin,^a Ekaterina P. Altova,^a Nikolai M. Karasev,^a Orudzh G. Nabiev,^b Lev V. Vilkov ‡^a and Heinz Oberhammer^c

Author affiliations

* Corresponding authors

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow 119991, Russia
E-mail: dorofeeva@phys.chem.msu.ru

^b N.N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Kosygin St. 4, Moscow 119991, Russia

^c Institut für Physikalische und Theoretische Chemie, Universität Tübingen, 72076 Tübingen, Germany

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_azidogauche 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.

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

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Supplementary files

Experimental details of GED experiment (Table S1); experimental intensity curves (Table S2, Fig. S1, Fig. S2); equilibrium distribution of AMP conformers (Table S3); molecular structure of gauche– anti and anti– gauche conformers of AMP obtained by gas-phase electron diffraction and quantum chemical calculations (Tables S4 and S5); vibrational amplitudes and vibrational corrections (Tables S6 and S7), correlation matrix (Table S8), experimental coordinates of atoms (Table S9). PDF (265K)

Article information

DOI: https://doi.org/10.1039/C0CP00894J
Article type: Paper
Submitted: 16 Jun 2010
Accepted: 14 Oct 2010
First published: 07 Dec 2010

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Phys. Chem. Chem. Phys., 2011,13, 1490-1498

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

O. V. Dorofeeva, A. V. Mitin, E. P. Altova, N. M. Karasev, O. G. Nabiev, L. V. Vilkov and H. Oberhammer, Phys. Chem. Chem. Phys., 2011, 13, 1490 DOI: 10.1039/C0CP00894J

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Physical Chemistry Chemical Physics

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

Abstract

Supplementary files

Article information

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

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