1-Fluoro-2-hydrostibatrane |
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| Authors: | M G Voronkov V A Pestunovich A I Albanov G A Kuznetsova É A Selbst V P Baryshok |
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| Institution: | (1) A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Russia;(2) Irkutsk State Pedagogical University, Russia |
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| Abstract: | 1-Fluoro-2-hydrostibatrane was synthesized by the reaction of antimony trifluoride with triethanolamine. The molecular structure of the compound was studied by X-ray diffraction and multinuclear magnetic resonance. The coordination polyhedron of the Sb atom is intermediate between a distorted tetrahedron (AX4E type of molecule) and a tetrahedral pyramid (AX4DE type of molecule). Diastereotopism of the geminal protons of each methylene group in the half-rings of the heterocycle, observed in the NMR spectra, vanishes at 65°C because of reversible cleavage of the N → Sb coordination bond and inversion of the nitrogen atom. The chemical environment of the OCH2 and NCH2 protons of the heterocycle and 2-hydroxyethyl protons is averaged due to the fast prototropic tautomerism at 75–120°C (in DMSO-d 6). |
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| Keywords: | 1-fluoro-2-hydrostibatrane synthesis molecular structure 1H and 13C NMR diastereotopism of protons inversion of the nitrogen atom prototropic tautomerism |
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