TY - JOUR
T1 - Achiral-to-chiral transition in benzil solidification: Analogies with racemic conglomerates systems showing deracemization
AU - El-Hachemi, Zoubir
AU - Arteaga, Oriol
AU - Canillas, Adolf
AU - Crusats, Joaquim
AU - Sorrenti, Alessandro
AU - Veintemillas-Verdaguer, Sabino
AU - Ribo, Josep M.
PY - 2013/7/1
Y1 - 2013/7/1
N2 - 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.
AB - 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.
KW - asymmetric amplification
KW - chirality
KW - circular dichroism
KW - phase transition
KW - racemic conglomerates
U2 - 10.1002/chir.22161
DO - 10.1002/chir.22161
M3 - Article
VL - 25
SP - 393
EP - 399
IS - 7
ER -