Solution-Phase Racemization in the Presence of an Enantiopure Solid Phase

✍ Scribed by Cristobal Viedma; Bastiaan J. V. Verkuijl; José E. Ortiz; Trinidad de Torres; Richard M. Kellogg; Donna G. Blackmond

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 300 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200902983

✦ Synopsis

Abstract

Solution‐phase racemization drives the evolution of single chirality in the solid phase by the “chiral amnesia” process first described by Viedma. The current investigations lay the basis for a better understanding of the mechanism of the solid‐phase deracemization by uncoupling the chemical rate processes associated with the interconversion of enantiomers in the solution phase from the physical processes associated with solution–solid phase transfer via dissolution and reaccretion of molecules onto crystals. In addition, the enantiomer concentration profiles presented in this work, together with an analytical treatment of the racemization process in the presence of excess enantiopure solid, unequivocally reconfirm the validity of the Meyerhoffer double solubility rule for systems under solution racemization conditions.