Abstract
The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.