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Updated: Oct 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Structural metrics relationships in covalently bonded organic azides
1CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, Avenue de la Terrasse, 91198 Gif Sur Yvette CEDEX, France. luba.tchertanov@icsn.cnrs-gif.fr
Abstract:
Geometrical parameters of covalently bonded organic azides have been analysed using X-ray structural data retrieved from the Cambridge Structural Database. The RNNN fragment geometry shows some important general features: (i) a preference for a trans C(s) configuration; (ii) bending of the N-N-N unit; (iii) substantially different N-N bond lengths in the azide group. Electron-density redistribution within the covalently bonded azide group (relative to that in the isolated azide anion) promotes the capacity of the terminal azide N atom to form hydrogen bonds.
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