Abstract
N-benzylcinchonidinium bromide, C26H29N2O+·Br-, with the systematic name (R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol bromide, is a quaternary ammonium salt of the cinchona alkaloid cinchonidine. This salt is widely used as a chiral phase-transfer catalyst and chiral resolution agent. Both classical and non-classical hydrogen-bonding interactions, as well as anion effects have been shown to play key mechanistic roles in the catalysis of cinchona alkaloids. In an effort to understand the effects of water on these intermolecular interactions, the structures of anhydrous N-benzylcinchonidinium bromide, (I), and the sesquihydrate, C26H29N2O+·Br-·1.5H2O, (II), were determined.
Original language | English |
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Pages (from-to) | 594-598 |
Number of pages | 5 |
Journal | Acta Crystallographica Section E: Crystallographic Communications |
Volume | 78 |
Issue number | Pt 6 |
DOIs | |
State | Published - Jun 1 2022 |
Bibliographical note
Publisher Copyright:© 2022 Janzen et al.
Keywords
- crystal structure
- hydrogen bonding
- quaternary ammonium salt of cinchonidine
ASJC Scopus subject areas
- General Chemistry
- General Materials Science
- Condensed Matter Physics