Crystal structures of anhydrous and hydrated N-benzyl-cinchonidinium bromide

Acta Crystallogr E Crystallogr Commun. 2022 May 17;78(Pt 6):594-598. doi: 10.1107/S2056989022005096. eCollection 2022 Jun 1.

ABSTRACT

N-benzyl-cinchonidinium bromide, C26H29N2O+·Br-, with the systematic name (R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabi-cyclo-[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 inter-actions, 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 inter-molecular inter-actions, the structures of anhydrous N-benzyl-cinchonidinium bromide, (I), and the sesquihydrate, C26H29N2O+·Br-·1.5H2O, (II), were determined.

PMID:36072147 | PMC:PMC9431800 | DOI:10.1107/S2056989022005096

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