Premium
Achiral‐to‐Chiral Transition in Benzil Solidification: Analogies with Racemic Conglomerates Systems Showing Deracemization
Author(s) -
ElHachemi Zoubir,
Arteaga Oriol,
Canillas Adolf,
Crusats Joaquim,
Sorrenti Alessandro,
VeintemillasVerdaguer Sabino,
Ribo Josep M.
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22161
Subject(s) - benzil , chemistry , chirality (physics) , enantiomer , grinding , crystallite , conglomerate , crystal (programming language) , atropisomer , crystallography , stereochemistry , organic chemistry , chiral symmetry , catalysis , metallurgy , physics , materials science , quantum mechanics , computer science , nambu–jona lasinio model , programming language , quark , paleontology , biology , sedimentary rock
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.