Abstract

In this paper, macroscopic chiral symmetry breaking refers to as the process in which a mixture of enantiomers departs from 50–50 symmetry to favor one chirality, resulting in either a scalemic mixture or a pure enantiomer. In this domain, crystallization offers various possibilities, from the classical Viedma ripening or Temperature Cycle-Induced Deracemization to the famous Kondepudi experiment and then to so-called Preferential Enrichment. These processes, together with some variants, will be depicted in terms of thermodynamic pathways, departure from equilibrium and operating conditions. Influential parameters on the final state will be reviewed as well as the impact of kinetics of the R ⇔ S equilibrium in solution on chiral symmetry breaking. How one can control the outcome of symmetry breaking is examined. Several open questions are detailed and different interpretations are discussed.

Highlights

  • Chiral Discrimination between Pairs of Enantiomers in the Solid StateTwo behaviors of the R–S system regarding racemization need to be distinguished. In the first case, the two enantiomers do not interconvert under the operating condition or in the time scale of the experiment

  • In this paper, macroscopic chiral symmetry breaking refers to as the process in which a mixture of enantiomers departs from 50–50 symmetry to favor one chirality, resulting in either a scalemic mixture or a pure enantiomer

  • Induced by deracemization variants where single flux or several fluxes of energy pass through a suspension)

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Summary

Chiral Discrimination between Pairs of Enantiomers in the Solid State

Two behaviors of the R–S system regarding racemization need to be distinguished. In the first case, the two enantiomers do not interconvert under the operating condition or in the time scale of the experiment. In the latter case, if there is no in the solid state, the chiral discrimination in this single solid phase is very poor. There is the miscibility gap in the solid state, the chiral discrimination in this single solid phase is very poor. The latter case is by far the most stoichiometric intermediate solid phase, called the “racemic compound” (Figure 1D) The latter case popular: it accounts for 90–95% of all derivatives of a given couple of enantiomers. From a racemic compound at low temperature, a stable conglomerate can be obtained at higher temperature through a three-phase peritectoid invariant [1]. The chiral discrimination in the solid state continuously as the two symmetrical solvus curves become more apart and towards a low temperature. Named lamellar conglomerates, whichnot should not be confused with racemic compounds

Equilibrium in Solution
Macroscopic Spontaneous Chiral Symmetry Breaking Induced by Crystallization
Isoindolinones that could deracemized
Control of Macroscopic Chiral Symmetry Breaking by Means of Crystallization
11. Impurity
12. Second-Order
Conclusions
Crystallization
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