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Related Concept Videos

SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Racemic Mixtures and the Resolution of Enantiomers02:30

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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

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It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Radical Halogenation: Stereochemistry01:33

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Spontaneous Mirror-Symmetry Breaking Destabilizes Racemates: A Route to Homochirality and Reversed Chemical

Josep M Ribó1, Jean-Claude Micheau2, Thomas Buhse3

  • 1Department of Organic and Inorganic Chemistry, Institute of Cosmos Science (IEEC-UB), University of Barcelona, Barcelona, E-08028, Catalonia, Spain.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|October 10, 2025
PubMed
Summary

Spontaneous mirror-symmetry breaking (SMSB) requires more than simple autocatalysis. It emerges from destabilizing a racemate via coupled enantioselective reactions, leading to unique chemical states.

Keywords:
entropy productionfar‐from‐equilibrium thermodynamicsspontaneous mirror‐symmetry breaking reaction networkssystems chemistry

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Area of Science:

  • Chemistry
  • Chemical Kinetics
  • Origin of Life Studies

Background:

  • Spontaneous mirror-symmetry breaking (SMSB) is crucial for understanding molecular chirality.
  • Existing models often rely on autocatalytic dynamics for enantiomeric excess (ee) emergence.
  • The precise mechanisms driving SMSB, especially in far-from-equilibrium conditions, remain debated.

Purpose of the Study:

  • To re-evaluate models and experiments related to spontaneous mirror-symmetry breaking (SMSB).
  • To elucidate the fundamental dynamics required for the emergence of enantiomeric excesses (ee).
  • To investigate the role of autocatalysis and coupled reactions in achieving chiral states.

Main Methods:

  • Revisiting and analyzing existing theoretical models and experimental data on SMSB.
  • Applying stoichiometric network analysis to understand reaction dynamics.
  • Investigating the interplay between autocatalysis and enantioselective reactions.

Main Results:

  • All revisited models exhibit first-order autocatalytic dynamics for ee emergence.
  • First-order autocatalysis alone is insufficient to drive SMSB.
  • The emergence of scalemic nonequilibrium stationary states (NESS) results from racemate destabilization via coupled reactions.
  • SMSB is identified as a signature of a bifurcation scenario leading to scalemic NESSs.

Conclusions:

  • SMSB necessitates the coupling of autocatalysis with other enantioselective reactions to destabilize racemates.
  • Autocatalytic networks are key to interpreting changes in chemical selectivity for competitive replicators under nonequilibrium conditions.
  • These findings offer insights into the chemical basis of chirality relevant to prebiotic chemistry and asymmetric synthesis.