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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

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.
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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...
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Molecules with Multiple Chiral Centers02:25

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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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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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Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

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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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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Chiral recognition in separation science - an update.

Gerhard K E Scriba1

  • 1Friedrich Schiller University Jena, Department of Pharmaceutical/Medicinal Chemistry, Philosophenweg 14, 07743 Jena, Germany.

Journal of Chromatography. A
|June 20, 2016
PubMed
Summary
This summary is machine-generated.

Understanding chiral molecule recognition in analytical enantioseparations is key. This review covers binding mechanisms of various chiral selectors, focusing on interactions like hydrogen bonds and halogen bonding.

Keywords:
Chiral recognition mechanismChiral selectorComplex formationEnantiomer separation

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Area of Science:

  • Analytical Chemistry
  • Chiral Separations
  • Molecular Recognition

Background:

  • Stereospecific recognition of chiral molecules is crucial in life sciences and chemistry.
  • Analytical enantioseparations rely on transient diastereomeric complex formation.
  • Interactions involved include hydrogen bonds, ionic, van der Waals, π-π, and recently, halogen bonding.

Purpose of the Study:

  • To review recent advances (2012-2016) in understanding chiral selector-selectand binding mechanisms.
  • To highlight the role of various interactions in analytical enantioseparations.
  • To provide an overview of diverse chiral selector types.

Main Methods:

  • Literature review of studies on chiral selectors and enantioseparation mechanisms.
  • Analysis of contributions from spectroscopic techniques (NMR) and X-ray crystallography.
  • Inclusion of molecular modeling for structural visualization.

Main Results:

  • Detailed examination of binding mechanisms for numerous chiral selectors.
  • Identification of key interactions driving enantioseparation.
  • Compilation of recent developments in polysaccharide derivatives, cyclodextrins, cyclofructans, and more.

Conclusions:

  • Recent research has significantly advanced the understanding of chiral recognition mechanisms.
  • A wide array of chiral selectors and interaction types are employed in enantioseparation.
  • Further research continues to refine the understanding of these complex molecular interactions.