Quininium Malates: Partial Chiral Discrimination via Diastereomeric Salt Formation

  • NB Báthori
  • A Jacobs
  • LR Nassimbeni
  • BK Sebogisi
Keywords: Chiral discrimination, diastereomeric salt, quinine.

Abstract

Quinine was employed as a resolving agent for racemic malic acid. The resultant product was a quininium salt containing 75 % of the D-malate anion. Quinine was also crystallized with pure L- and D-malic acids and the structures of the resulting diastereomeric salts were elucidated. The crystal packings were analyzed in terms of their non-bonded interactions and the conformation of the quinine, which was compared with other quinine structures recorded in the Cambridge Structural Database. The results indicate that the mechanism of enantiomeric resolution is reliant upon hydrogen bonded interactions.

KEYWORDS: Chiral discrimination, diastereomeric salt, quinine.

Published
2015-09-21
Section
Articles

Journal Identifiers


eISSN: 0379-4350