Toward the computational design of diastereomeric resolving agents: An experimental and computational study of 1-phenylethylammonium-2-phenylacetate derivatives

Low-temperature single crystal or powder X-ray diffraction is used to characterize the crystal structures, including two new polymorphs, of three diastereomerically related salt pairs formed by 1-phenylethylammonium with 2-phenylpropanoate, 2-phenylbutyrate and mandelate ions. The findings demonstrate that the stability difference of the diastereomeric salt pairs of three 1-phenylethylammonium-2-phenylacetate derivatives is related to their resolution efficiency and varies considerably, despite the similarity in their molecular structure and hydrogen-bonding motifs.