Crystal structures of anhydrous and hydrated N-benzylcinchonidinium bromide

Daron E. Janzen, Maya S. Butler, Eric W. Reinheimer, S. Parkin

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)594-598
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume78
Issue numberPt 6
DOIs
StatePublished - 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

  • Chemistry (all)
  • Materials Science (all)
  • Condensed Matter Physics

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