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Updated: May 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Benzylammonium hepta-noate-hepta-noic acid (1/1)
1BP Institute and Department of Chemistry, University of Cambridge, Cambridge CB3 0EZ, England.
Abstract:
The title salt, C7H10N(+)·C7H13O2(-)·C7H14O2, is an unusual 2:1 stoichiometric combination of two carb-oxy-lic acid mol-ecules and one amine. Although there are crystal structures of a number of 1:1 complexes reported in the literature, 2:1 acid amine complexes are rather uncommon. In this case, a proton is transferred between one acid mol-ecule and the amine to give an acid anion and an ammonium cation whilst the other carb-oxy-lic acid remains protonated. The species inter-act strongly via electrostatic forces and hydrogen bonds. In addition we note that the N atom of the ammonium group makes four close contacts to surrounding O atoms. Three of these are hydrogen bonds with neighbouring acid anions while the fourth does not involve a hydrogen atom but is directed towards the carbonyl O atom of the protonated acid. Each of the acid anion O atoms accepts two hydrogen bonds from adjacent N atoms. There is also evidence of short C-H⋯O contacts. There is disorder (occupancy ratio 0.51:0.49) in the alkyl chain of one of the carb-oxy-lic acid mol-ecules.
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