Achiral‐to‐Chiral Transition in Benzil Solidification: Analogies with Racemic Conglomerates Systems Showing Deracemization |
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| Authors: | Zoubir El‐Hachemi Oriol Arteaga Adolf Canillas Joaquim Crusats Alessandro Sorrenti Sabino Veintemillas‐Verdaguer Josep M Ribo |
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| Institution: | 1. Departament de Química Orgànica, Universitat de Barcelona (IEEC‐UB), , Barcelona, Catalonia, Spain;2. Institut de Ciències del Cosmos (ICC), Universitat de Barcelona (IEEC‐UB), , Barcelona, Catalonia, Spain;3. Departament de Física Aplicada, Universitat de Barcelona, , Barcelona, Catalonia, Spain;4. Institut de Nanociència i Nanotecnologia (IN2UB), Universitat de Barcelona, , Barcelona, Catalonia, Spain;5. New York University, Department of Chemistry, , New York, NY, USA;6. Departament de Química, Facultat de Ciències, Universitat Autònoma de Barcelona, , Bellaterra, Catalonia, Spain;7. Centro de Astrobiología (CSIC‐INTA), , Torrejón de Ardoz, Madrid, Spain |
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| Abstract: | Experimental results show that benzil (1,2‐diphenyl‐1,2‐ethanedione), an achiral compound that crystallizes as a racemic conglomerate, yields by solidification polycrystalline scalemic mixtures of high enantiomeric excesses. These results are related to those previously reported in this type of compounds on deracemizations of racemic mixtures of crystal enantiomorphs obtained by wet grinding. However, the present results strongly suggest that these experiments cannot be explained without taking into account chiral recognition interactions at the level of precritical clusters. The conditions that would define a general thermodynamic scenario for such deracemizations are discussed. Chirality 25:393–399, 2013. © 2013 Wiley Periodicals, Inc. |
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| Keywords: | asymmetric amplification chirality circular dichroism phase transition racemic conglomerates |
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