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Related Concept Videos

Chirality02:25

Chirality

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...
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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
08:51

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Published on: August 18, 2017

Can monoatomic xenon become chiral?

K Bartik1, M El Haouaj, M Luhmer

  • 1Laboratoire de Chimie Organique CP 165/64, Université Libre de Bruxelles, 50 av FD Roosevelt, 1050 Bruxelles, Belgium.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|May 23, 2013
PubMed
Summary

A chiral host molecule, cryptophane-A, was shown to induce chirality in noble gases. This finding was confirmed using xenon-129 nuclear magnetic resonance spectroscopy.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Published on: March 24, 2018

Area of Science:

  • Supramolecular Chemistry
  • Nuclear Magnetic Resonance Spectroscopy
  • Chirality Studies

Background:

  • Chirality is a fundamental property in chemistry and biology, typically associated with organic molecules.
  • Noble gases are generally considered achiral due to their spherical symmetry.
  • Host-guest chemistry explores the interactions between molecules and their encapsulating structures.

Purpose of the Study:

  • To investigate whether a chiral host can induce chirality in an achiral guest molecule, specifically a noble gas.
  • To demonstrate the transfer of chirality from a host to a guest at the atomic level.
  • To explore novel applications of supramolecular chemistry in fundamental property manipulation.

Main Methods:

  • Synthesis and characterization of cryptophane-A (1) as the chiral host.
  • Nuclear Magnetic Resonance (NMR) spectroscopy using xenon-129 ((129)Xe NMR) to probe the host-guest interactions.
  • Utilizing a chiral chemical shift reagent to differentiate enantiotopic environments.

Main Results:

  • Cryptophane-A successfully encapsulated xenon atoms.
  • (129)Xe NMR spectra showed distinct signals in the presence of the chiral host, indicating the induction of a chiral environment around the xenon atom.
  • The chiral chemical shift reagent further confirmed the enantiomeric discrimination of the xenon atoms within the host.

Conclusions:

  • A monoatomic noble gas, xenon, can be rendered chiral when encapsulated within the chiral host cryptophane-A.
  • This study expands the concept of chirality to include simple atomic species, challenging previous assumptions.
  • The findings open new avenues for studying chiral recognition and enantioselective interactions involving noble gases.