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Related Concept Videos

Chirality02:25

Chirality

24.2K
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 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...
5.7K
Chirality in Nature02:30

Chirality in Nature

13.4K
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.
13.4K
Prochirality02:05

Prochirality

3.8K
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...
3.8K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

11.6K
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...
11.6K
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

1.7K
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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Related Experiment Video

Updated: Jun 27, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Chiral Thianthrenes.

M John Plater1, William T A Harrison1

  • 1Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UK.

International Journal of Molecular Sciences
|April 27, 2024
PubMed
Summary
This summary is machine-generated.

Chiral sulfoxides were analyzed for absolute configuration and stability. X-ray crystallography confirmed diastereomeric sulfoxides are stable in solution, not interconverting as previously hypothesized.

Keywords:
chiral sulfoxideconfigurationdiastereoisomerdithiinresolutionsulfoxidethianthrene

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Crystallography

Background:

  • Sulfoxides are known to undergo racemization or epimerization under certain conditions.
  • Previous studies have suggested potential interconversion of diastereomeric sulfoxides in solution.
  • Thianthrene derivatives offer a unique scaffold for studying chiral sulfoxide behavior.

Purpose of the Study:

  • To determine the absolute configuration and solution stability of two thianthrene chiral sulfoxides.
  • To verify whether diastereomeric sulfoxides interconvert in solution.
  • To establish reliable separation methods for these chiral compounds.

Main Methods:

  • X-ray single-crystal structure determination was employed to ascertain absolute configuration.
  • Thin Layer Chromatography (TLC) and flash chromatography on silica were used for separation and analysis.
  • Spectroscopic methods were implicitly used for compound characterization (though not detailed in abstract).

Main Results:

  • The absolute configurations of the two thianthrene chiral sulfoxides were definitively determined.
  • The diastereomeric sulfoxides were confirmed to be stable in solution and did not interconvert.
  • Successful separation of the diastereomers was achieved using flash chromatography, despite challenging co-elution (back-to-back spots).
  • Pure separated compounds maintained their integrity as single spots on TLC plates in solution.

Conclusions:

  • The study provides concrete evidence against the interconversion of these specific diastereomeric thianthrene sulfoxides in solution.
  • X-ray crystallography is a robust method for determining absolute configuration in such systems.
  • Flash chromatography on silica is an effective technique for separating challenging diastereomeric sulfoxides.