title: Conformational and H-bonding preferences for facile racemate crystallization of ribose.
abstract: Recalcitrant crystallization and syrup formation are frequent features of natural sugars. This is the case of D-ribose, yielding low-quality crystals of mixed α- and β-pyranose anomers. However, large crystals of DL-ribose can be grown easily. The crystal structures of stable D-ribose forms I and II as well as DL-form II have been analyzed in terms of their compatibility with the molecular aggregation. The comparison of the potential energy of all conformers and their OH···O hydrogen-bonding patterns is consistent with the preferential racemate crystallization in terms of departures from the optimized isolated ribose molecule and its directional interactions. This analysis is aimed at rationalizing the interplay between the molecular structure and spontaneous crystallization of chiral compounds.
authors.affiliation: Department of Materials Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland.
authors.forename: Ewa
authors.initials: E
authors.lastname: Patyk
authors.forename: Andrzej
authors.initials: A
authors.lastname: Katrusiak
keywords: chiral aggregation; enantiomers; monosaccharide; racemic ribose; solid state conformers