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Related Concept Videos

Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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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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It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
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On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Chirality in Nature02:30

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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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Racemic Mixtures and the Resolution of Enantiomers02:30

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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...
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Updated: Mar 23, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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An exceptional 5:4 enantiomeric structure.

Erin Wachter1, Edith C Glazer1, Sean Parkin1

  • 1Department of Chemistry, University of Kentucky, 505 Rose St, Lexington, KY 40506-0055, USA.

Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
|April 7, 2016
PubMed
Summary
This summary is machine-generated.

Crystallizing a complex ruthenium cation revealed an unusual structure with nine unique ions and multiple solvent molecules. This complexity explains the challenges in growing these crystals, highlighting intricate molecular organization.

Keywords:
Z′ = 9anomalous racemateunbalanced crystallization

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Area of Science:

  • Coordination Chemistry
  • Crystallography
  • Materials Science

Background:

  • Resolvable chiral cations are crucial for developing advanced materials and asymmetric synthesis.
  • Understanding the crystal structures of complex coordination compounds is key to controlling their properties.
  • Racemic solutions often present challenges in obtaining well-defined crystalline structures.

Purpose of the Study:

  • To elucidate the crystal structure of the PF6(-) salt of a specific resolvable ruthenium cation.
  • To investigate the packing, symmetry, and conformational details of the complex cation and its counterions.
  • To understand the factors contributing to the difficulty in crystallizing this compound.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • Detailed analysis of the asymmetric unit, including ion and solvent molecule arrangements.
  • Examination of cation conformation, symmetry elements, and twinning to understand structural complexity.

Main Results:

  • The crystal structure (space group P1) exhibits translational symmetry only, with nine independent ions and numerous solvent molecules (acetone, diethyl ether, water).
  • Cations form alternating layers with anions and solvent molecules; cation conformation is distorted by methyl substituents.
  • An 80:20 inversion twinning ratio suggests imperfect transmission of enantiomeric preference between layers, linked to the nine independent formula units and a 4:5 enantiomer ratio.

Conclusions:

  • The crystal structure is exceptionally complex, featuring multiple independent ions and solvent molecules, which explains the difficulty in crystal growth.
  • The arrangement of cations and anions/solvents, along with the observed twinning, provides insights into chiral recognition and transmission in the solid state.
  • This study highlights the challenges and intricacies involved in crystallizing complex, chiral coordination compounds.