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Related Concept Videos

Chirality02:25

Chirality

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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

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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.
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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...
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Prochirality02:05

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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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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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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...
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A Micropatterning Assay for Measuring Cell Chirality
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Comment on "Bad Language": Resolving some Ambiguities about Chirality.

Michel Petitjean1,2

  • 1Université Paris Diderot, CMPLI, INSERM ERL U1133 (BFA, CNRS UMR 8251), France.

Angewandte Chemie (International Ed. in English)
|April 16, 2020
PubMed
Summary

This comment clarifies concepts in chirality, adding new insights to Dunitz's "Bad Language" essay. It aims to reduce ambiguities and misconceptions surrounding molecular chirality.

Keywords:
chiralitylanguagestereochemistrysymmetry

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Area of Science:

  • Chemistry
  • Stereochemistry

Background:

  • This work comments on Dunitz's essay "Bad Language."
  • It addresses the topic of chirality and its associated terminology.

Discussion:

  • Introduces novel elements to the ongoing discussion on chirality.
  • Aims to resolve ambiguities and challenge preconceived notions in the field.

Key Insights:

  • Provides new perspectives on understanding chirality.
  • Contributes to a clearer conceptual framework for stereochemistry.

Outlook:

  • Encourages further refinement of language and concepts in chirality.
  • Promotes a more precise understanding of molecular asymmetry.