Quasiracemic materials consist of pairs of left and right-handed chemically distinct molecules. Because the complementary shapes of the quasienantiomeric components provide the primary structural driving force for quasiracemates formation, these systems offer an important opportunity to examine the role of molecular topology in molecular recognition. Our previous investigations in this area optimized quasiracemate formation by designing components with similar spatial properties. Here we report how systems with increased crystal lattice stabilization affect the cocrystal assembly of the quasiracemic components. The added stability in crystal packing is achieved by constructing molecular frameworks that are spatially larger (naphthyl amides) or promote robust hydrogen-bonded assemblies (amino acids and caboxylamides). Data collected from these materials using X-ray crystallography, thermal analysis methods, and lattice energy calculations provide important insight into how these new quasiracemate scaffolds facilitate greater structural variance of the component substituents during the pairwise assembly of quasienantiomers. Outcomes from this study also highlight a broader structure space towards the identification of new isostructural building blocks and important molecular relationships for quasiracemate crystallization.

Quasiracemic assembly from spatially diverse quasienantiomeric components

ACS Spring Meeting 2021

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