Isotopically-Directed Symmetry Breaking and Enantioenrichment in Attrition-Enhanced Deracemization.

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ID: 92609
2020
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Abstract
TThe evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enanti-oenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or 13C version, and the protio version is consistently favored over the 13C version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points. Understanding the origin of this iso-tope bias provides fundamental clues about overcoming stochastic behavior to direct the stereochemical outcome in attrition-enhanced deracemization processes. The energy required for breaking symmetry with chiral bias is compared for this near-equilibrium AED process and t the far-from-equilibrium Soai autocatalytic reaction. Implications for the origin of biological homochirality are discussed.
Reference Key
murray2020isotopicallydirectedjournal Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Murray, James I;Sanders, Jacob N;Richardson, Paul F;Houk, K N;Blackmond, Donna G;
Journal Journal of the American Chemical Society
Year 2020
DOI
10.1021/jacs.9b11422
URL
Keywords
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