Case Study on the Interpretation of Crystal Structures Inducing Preferential Enrichment Based on the Graph Set Analysis of Hydrogen Bond Motifs

The
hydrogen bond motifs in the racemic crystals of the first-generation
of chiral organic compounds, which showed a good to excellent preferential
enrichment (PE) phenomenon, were rationalized by graph set analysis
in terms of the selective dissolution of the excess one enantiomer
from the transformed disordered crystals. By comparing these motifs
with those of several analogous compounds incapable of showing PE,
the graph sets necessary to induce PE with respect to the first-generation
compounds were unveiled. On the basis of this graph set study, compounds
with a new type of crystal structure (β1-form) and
graph set which can induce PE have been revealed.