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Related Concept Videos

Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
Stereoisomers02:32

Stereoisomers

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 restricted...
Isomerism02:43

Isomerism

Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

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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Related Experiment Video

Updated: Jun 8, 2026

Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy
08:49

Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy

Published on: December 1, 2023

Complementing ultrafast shape recognition with an optical isomerism descriptor.

Ting Zhou1, Karine Lafleur, Amedeo Caflisch

  • 1Department of Biochemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.

Journal of Molecular Graphics & Modelling
|October 2, 2010
PubMed
Summary
This summary is machine-generated.

We developed a novel descriptor for optical isomerism using a mixed product of three vectors. This method efficiently distinguishes mirror-image isomers, including enantiomers and conformational isomers, by assigning opposite signs.

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Related Experiment Videos

Last Updated: Jun 8, 2026

Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy
08:49

Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy

Published on: December 1, 2023

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Area of Science:

  • Computational chemistry
  • Molecular modeling
  • Stereochemistry

Background:

  • Distinguishing between optical isomers (enantiomers) and conformational isomers is crucial in chemistry.
  • Existing methods like Ultrafast Shape Recognition (USR) struggle to differentiate enantiomers due to their reliance on distance-based comparisons.
  • A need exists for robust and efficient descriptors capable of accurately identifying stereoisomers.

Purpose of the Study:

  • To introduce a new descriptor for optical isomerism based on the mixed product of three vectors.
  • To demonstrate the descriptor's efficiency and robustness in distinguishing between mirror-image isomers.
  • To evaluate the descriptor's utility in complementing existing shape recognition methods for database searching.

Main Methods:

  • A novel descriptor is formulated using the mixed product of three vectors spanning four molecular locations.
  • The descriptor's sign is analyzed to differentiate between isomers and their mirror images.
  • Comparison is made between the new descriptor, Ultrafast Shape Recognition (USR), and Gaussian molecular volume overlap for accuracy and completeness.

Main Results:

  • The proposed descriptor effectively distinguishes optical isomers and conformational isomers by yielding opposite sign values.
  • The descriptor does not require molecular superposition, enhancing its computational efficiency.
  • When combined with USR, the descriptor improves the ability to identify enantiomers, overcoming a limitation of USR alone.

Conclusions:

  • The mixed product descriptor offers an efficient and robust method for analyzing optical isomerism.
  • This descriptor serves as a valuable complement to distance-based shape recognition methods like USR.
  • The approach enhances stereochemical discrimination in molecular databases and computational analyses.