4.6 Article

Chiral amnesia as a driving force for solid-phase homochirality

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 12, Pages 3290-3295

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601463

Keywords

chiral resolution; chirality; crystal growth; crystallization; eutectic; phase rule

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The formation of a single homochiral solid phase from crystallization of achiral compounds has recently been under discussion. We show that the state of single solid-phase homochirality does not represent a more stable thermodynamic state than that of a racemate consisting of two separate homochiral solids. We introduce the term chiral amnesia as a more appropriate molecular-level description than chiral recognition to describe the driving force for establishing solid-phase homochirality in the case of achiral molecules that form chiral solids as well as in the case of rapidly racemizing enantiomers.

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