Although the title compound crystallizes as a stable conglomerate without any detectable solid solution, particles in the shape of single crystals grown from the racemic aqueous solution without stirring contain almost no enantiomeric excess. From stereoselective dissolution experiments carried out in a solution saturated with a single enantiomer, it is shown that the formation of these particles results from the epitaxial association of macroscopic homochiral lamellar fragments parallel to the {101} faces. This alternated 2D nucleation and growth process is shown to constitute an oscillating crystallization mechanism controlled by diffusion only. This is confirmed by the implementation of a gentle stirring of the mother liquor during the crystallization which led to crystals having a high enantiomeric excess. Molecular modeling investigations indicate that the epitaxial region can be described at a molecular level. The structure of two racemic compounds could be generated from this epitaxial zone.
Herein, we report the chiral symmetry breaking of 2-methoxy-1-naphthamide atropisomers through temperature cycling without the use of any racemization reagent. The racemization rate (k 1 ) controls the deracemization process when the cooling of the slurry is slow enough to keep the system close to equilibrium. The productivity appears proportional to the racemization rate (k 1 ) multiplied by the solubility.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.