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Related Concept Videos

Chirality02:25

Chirality

26.8K
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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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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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.
14.6K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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...
6.2K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

13.6K
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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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.8K
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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Related Experiment Video

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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Chirality determination in crystals.

Ángela Valentín-Pérez1, Patrick Rosa1, Elizabeth A Hillard1,2

  • 1Univ. Bordeaux, CNRS, Bordeaux-INP, ICMCB, UMR 5026, F-33600 Pessac, Cedex, France.

Chirality
|November 12, 2021
PubMed
Summary
This summary is machine-generated.

This review details solid-state chirality determination using X-ray diffraction for single crystals and bulk assemblies. It covers absolute structure principles, complexities like inversion twinning, and advanced techniques such as X-ray natural circular dichroism mapping.

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Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Chirality studies

Background:

  • Chirality determination is crucial in various scientific fields.
  • Solid-state chiral analysis presents unique challenges compared to solution-state methods.
  • X-ray diffraction is a powerful tool for structural elucidation.

Purpose of the Study:

  • To provide a tutorial review on solid-state chirality determination.
  • To emphasize the application of X-ray diffraction techniques.
  • To discuss challenges and advanced methods for chiral analysis in crystals.

Main Methods:

  • Summarizing principles of X-ray diffraction for absolute structure determination.
  • Illustrating complexities in chiral structures (kryptoracemates, scalemates, inversion twinning).
  • Discussing techniques for bulk crystallization chirality assessment, including X-ray natural circular dichroism mapping.

Main Results:

  • X-ray diffraction reliably determines absolute structure in single crystals.
  • Complex chiral phenomena like inversion twinning require careful analysis.
  • X-ray natural circular dichroism mapping offers a promising method for bulk chiral analysis.

Conclusions:

  • Solid-state chirality determination is achievable through various X-ray diffraction-based methods.
  • Understanding structural complexities is key for accurate chiral assignment.
  • Advanced techniques are emerging for analyzing chiral properties in bulk crystalline materials.