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Related Concept Videos

Chirality02:25

Chirality

24.3K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Chirality in Nature02:30

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
13.5K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

11.8K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
11.8K
Prochirality02:05

Prochirality

3.8K
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...
3.8K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.8K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
5.8K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.0K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Critical behavior in a chiral molecular model.

Pablo M Piaggi1, Roberto Car1,2, Frank H Stillinger1

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

The Journal of Chemical Physics
|September 15, 2023
PubMed
Summary
This summary is machine-generated.

Chiral molecules in liquid phases can spontaneously separate into D-rich and L-rich states, a phenomenon crucial for pharmaceutical manufacturing and potentially explaining biological homochirality.

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Area of Science:

  • Condensed-phase physics
  • Chiral molecular systems
  • Phase transitions

Background:

  • Chirality is fundamental in biological systems and pharmaceutical applications.
  • Understanding chiral molecule behavior in condensed phases is critical.
  • Previous models lacked detailed phase transition insights.

Purpose of the Study:

  • Investigate the condensed-phase behavior of chiral molecules.
  • Characterize the symmetry-breaking phase transition in a chiral model.
  • Explore mechanisms for chirality selection and biological homochirality.

Main Methods:

  • Molecular dynamics simulations of a chiral four-site model.
  • Determination of critical temperature using fourth-order Binder cumulant.
  • Analysis of finite-size scaling and free energy barriers.

Main Results:

  • Observed a second-order phase transition from supercritical racemic to subcritical enantiomerically enriched liquids.
  • Finite-size scaling aligns with the 3D Ising universality class.
  • Free energy barrier for enantiomer separation scales as N^(2/3), indicating surface dominance.

Conclusions:

  • The study reveals a mechanism for spontaneous chirality selection in liquids.
  • Increasing system size suppresses enantiomeric phase fluctuations, favoring homochirality.
  • This provides a potential explanation for biological homochirality and suggests external field effects.