Pseudosymmetry and chiral discrimination in optical resolution via diastereoisomeric salt formation. The crystal structures of (R)- and (S)-N-methylamphetamine bitartrates (RMERTA and SMERTA)

Abstract

The structures of the diastereoisomeric salts of (R)- and (S)-N-methylamphetamine bitartrates (RMERTA and SMERTA) have been determined by X-ray crystallography. Comparison of these crystal structures provides an insight into the mechanism of optical resolution via diastereoisomeric salt formation. The very small difference between the two crystal structures indicates that specific interactions such as CH⋯O interactions may play an important role in molecular recognition.