Cocrystal formation between chiral compounds: How cocrystals differ from salts

Géraldine Springuel, Koen Robeyns, Bernadette Norberg, Johan Wouters, Tom Leyssens

Research output: Contribution to journalArticlepeer-review

Abstract

A cocrystal screening of a series of chiral target compounds was performed in order to investigate the propensity for two optically active compounds to cocrystallize in an enantiospecific manner. Thirteen novel cocrystal systems were identified, out of which 11 are enantiospecific and two present a diastereomeric cocrystal pair, yielding a total of 15 novel cocrystals. Six of these are structurally characterized in this study. A meticulous search in the Cambridge Structural Database (CSD) has allowed expanding this study. The results led us to the conclusion that enantiospecific cocrystallization seems to be the common rule of thumb, as over 85% of cocrystal systems behave enantiospecifically. Directionality of the hydrogen bonding motifs is likely responsible for the cocrystals' predilection toward enantiospecificity, while salts are mainly stabilized by less directional electrostatic interactions, leading to the formation of diastereomeric pairs.

Original languageEnglish
Pages (from-to)3996-4004
Number of pages9
JournalCrystal Growth and Design
Volume14
Issue number8
DOIs
Publication statusPublished - 6 Aug 2014

Fingerprint Dive into the research topics of 'Cocrystal formation between chiral compounds: How cocrystals differ from salts'. Together they form a unique fingerprint.

Cite this