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Related Concept Videos

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...
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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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Prochirality

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 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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Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
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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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Updated: Jun 17, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Electrostatic chiral distinction: tetrahedral model dimers.

Sarit Garten1, P Ulrich Biedermann, Sid Topiol

  • 1Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem, Israel.

Chirality
|December 17, 2009
PubMed
Summary

Chiral distinction in chemistry is not fully understood. This study reveals that complex stability and contact points do not predict chiral distinction, suggesting new avenues for research.

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Area of Science:

  • Chemistry
  • Molecular Modeling
  • Stereochemistry

Background:

  • Chiral distinction is fundamental in chemistry, yet its underlying mechanisms remain incompletely understood.
  • Previous models suggested a minimal requirement of four-point interactions for chiral recognition.

Purpose of the Study:

  • To expand upon existing models of chiral distinction by investigating point charge systems.
  • To identify operative principles governing chiral distinction through systematic modeling.

Main Methods:

  • Development of chiral point charge model systems with defined symmetry characteristics.
  • Analysis of extensive constellations of diastereomeric complexes.
  • Evaluation of chiral distinction energy in relation to complex stability and interaction points.

Main Results:

  • All analyzed diastereomeric complexes exhibit a chiral distinction energy, irrespective of contact points.
  • Chiral distinction magnitude does not correlate with complex stability or the number of contact points.
  • Favorable interactions and ease of chiral distinction were found to be unrelated.

Conclusions:

  • Complex stability and interaction details are not reliable indicators for predicting chiral distinction.
  • Less symmetric systems may exhibit greater chiral distinction, though this requires further investigation.
  • The findings provide a foundation for developing more complex models to understand chiral distinction.