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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

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 different...
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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 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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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 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. The...
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In chromatography, a solute moves through a chromatographic column and tends to spread, forming a Gaussian-shaped band. The longer the solute spends in the column, the broader the band becomes. The broadening can lead to overlaps within the column, affecting separation effectiveness.
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An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation
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New resolution technologies controlled by chiral discrimination mechanisms.

Kenichi Sakai1, Rumiko Sakurai, Hiroyuki Nohira

  • 1R&D Division, Yamakawa Chemical Industry Co., Ltd., Kitaibaraki, 319-1541, Ibaraki, Japan, kenichi_sakai@tfc.toray.co.jp.

Topics in Current Chemistry
|April 23, 2013
PubMed
Summary

Optical resolution via crystallization, a classical technique, is crucial for producing enantiomerically pure compounds. This study introduces three novel methods to optimize chiral purity and identify resolving agents for industrial applications.

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Area of Science:

  • Chirality and stereochemistry
  • Crystallization science
  • Process chemistry

Background:

  • Optical resolution via crystallization is a long-established technique for obtaining enantiomerically pure compounds.
  • The diastereomeric salt formation method is widely applied in pharmaceutical, agrochemical, and liquid crystal industries.
  • Current process development relies on empirical procedures due to a lack of concrete theory for optimal resolution conditions.

Purpose of the Study:

  • To present three novel approaches for optical resolution via diastereomeric salt formation.
  • To enhance chiral purity and develop systematic methods for resolving agent selection.
  • To advance the understanding and application of crystallization-based chiral resolution.

Main Methods:

  • Chiral purity improvement through crystal habit modification using tailored chiral additives.
  • A new approach for identifying suitable resolving agents based on the space filler concept.
  • Chirality control achieved through dielectrically controlled resolution.

Main Results:

  • Demonstration of improved chiral purity via crystal habit modification.
  • Introduction of a novel space filler concept for effective resolving agent screening.
  • Exploration of dielectric control as a method for chirality manipulation during resolution.

Conclusions:

  • The presented novel approaches offer significant advancements over traditional empirical methods in optical resolution.
  • These methods provide a more theoretical and systematic basis for process development in chiral compound production.
  • The findings contribute to more efficient and predictable industrial-scale enantioseparation.