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Related Concept Videos

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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Chirality02:25

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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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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

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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 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.
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¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Advances in chiral analysis: from classical methods to emerging technologies.

Roberto Penasa1, Giulia Licini1, Cristiano Zonta1

  • 1Department of Chemical Sciences, Università degli Studi di Padova, via Marzolo 1, 35131 Padova, Italy. cristiano.zonta@unipd.it.

Chemical Society Reviews
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Summary
This summary is machine-generated.

Chirality analysis is crucial across sciences. This review covers methods for fast, reliable enantiomeric excess (ee) determination, from polarimetry to modern supramolecular probes, highlighting recent advancements.

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Area of Science:

  • Chirality and enantiomeric excess (ee) determination are vital in chemistry, pharmaceuticals, and materials science.
  • The study of stereoisomers and their separation is a key area of chemical research.

Background:

  • Chirality has a significant impact across diverse scientific disciplines.
  • Accurate enantiomeric excess determination is essential for many applications.
  • Existing methods for ee determination vary in speed, cost, and applicability.

Purpose of the Study:

  • To provide a comprehensive overview of methodologies for enantiomeric excess determination.
  • To highlight recent progress, advantages, and disadvantages of various techniques.
  • To indicate current trends in the field of chirality analysis.

Main Methods:

  • Review of historical techniques such as optical polarimetry.
  • Analysis of modern instruments and supramolecular probes for ee determination.
  • Discussion of techniques with general applicability and reduced analysis time/cost.

Main Results:

  • A broad spectrum of methods for enantiomeric excess determination is available.
  • Recent advancements offer improved speed, reliability, and applicability.
  • Each technique presents unique advantages and limitations.

Conclusions:

  • The field of enantiomeric excess determination is continuously evolving.
  • Ongoing research aims for more versatile, faster, and cost-effective analytical techniques.
  • Understanding current trends is key for future developments in chirality analysis.