Quasiracemic materials have proven useful in examining the role of molecular topology in the landscape of molecular recognition profiles. Because the construction of quasiracemates only necessitates the pairwise use of structurally similar right and left-handed molecules (i.e., quasienantiomers), this approach to supramolecular assembly offers considerable flexibility beyond conventional studies that target specific non-bonded contacts or chemical classes. This presentation examines how a homologous family of chiral benzoyl amino acids create stabilized crystalline lattices that promote and easily accommodate quasienantiomers of greater structural diversity. For these systems, cocrystallization is accomplished by use of the complementary shapes of the components and increased stabilization by an extensive network of N-H…O and O-H…O hydrogen bond motifs. Crystallographic studies and lattice energy determinations draw attention to pairing quasienantiomers with significantly large functional group differences (e.g., H/I and F/CF3) and how these systems readily assemble and mimic the crystal packing and energy profiles that correspond to the racemic counterparts.

Targeted structural diversity in quasiracemic assemblies

ACS Spring 2022

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