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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Cinchoninium L-tartrate tetrahydrate
R Puliti1, C A Mattia, A De Fazio
1Istituto Chimica Biomolecolare CNR, Via Campi Flegrei 34, Ex Olivetti Fabbricato 70, I-80078 Pozzuoli, Napoli, Italy. puliti@chemistry.unina.it
Abstract:
The title compound, (3R,4S,8R,9S)-cinchoninium (2R,3R)-tartrate tetrahydrate, C19H23N2O+*C4H5O6-*4H2O, is a hydrated salt of cinchonine. In the cinchoninium cation, the geometry around the quinuclidinic N atom is typical of a protonated N atom, and the bond lengths and angles in the tartrate moiety clearly indicate the mono-ionized form. The relative orientation of the quinoline and quinuclidine systems is that most frequently observed in structures of cinchona salts and corresponds to one of the energy minima calculated for this type of molecule in the gas phase. An extended network of intermolecular hydrogen bonds spreads parallel to the bc plane separating apolar layers.

