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Related Concept Videos

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...
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,...
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...
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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Isomerism in Alkenes02:01

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...

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Related Experiment Video

Updated: May 29, 2026

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

Interstellar Stereoisomerism.

Víctor M Rivilla1, Miguel Sanz-Novo1, David San Andrés1

  • 1CSIC-INTA, Centro de Astrobiología (CAB), Ctra. de Ajalvir, km. 4, Torrejón de Ardoz, Madrid E-28850, Spain.

ACS Earth & Space Chemistry
|May 28, 2026
PubMed
Summary
This summary is machine-generated.

Stereoisomerism is key to interstellar molecular complexity. Observed ratios in space often defy thermodynamic predictions, indicating unique formation and transformation pathways are at play.

Keywords:
energyenvironmentshigher-energyinterstellarisomermoleculesratiosstereoisomerismstereoselective

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Last Updated: May 29, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

Area of Science:

  • Astrochemistry
  • Interstellar Medium (ISM) Research
  • Stereochemistry

Background:

  • Increasing detection of novel molecules in the ISM highlights the significance of stereoisomerism.
  • Stereoisomers, molecules with the same chemical formula but different spatial arrangements, contribute to molecular complexity.

Purpose of the Study:

  • To provide the first comprehensive overview of stereoisomerism in the interstellar medium.
  • To analyze observed stereoisomeric ratios (OSRs) and their implications for interstellar chemistry.

Main Methods:

  • Identification and analysis of 16 stereoisomeric pairs (13 conformational, 3 geometric) across diverse astrophysical environments.
  • Comparison of observed stereoisomeric ratios with thermodynamic expectations.

Main Results:

  • Stereoisomers were found in molecules with 5-12 atoms, with energy separations from ~10 K to 2667 K.
  • Observed stereoisomeric ratios (OSRs) varied widely (0.009-4) across different kinetic temperatures (7.5-300 K).
  • Many stereoisomers, especially in cold clouds or with large energy gaps, showed abundances exceeding equilibrium, defying thermodynamic predictions.

Conclusions:

  • Thermodynamics alone cannot explain interstellar stereoisomerism; stereoselective pathways (gas-phase, grain-surface), photoisomerization, and desorption processes are crucial.
  • Stereoisomeric ratios offer vital constraints on ISM chemical pathways and conditions.
  • Further research requires enhanced laboratory spectroscopy, quantum chemical studies, and stereochemistry-inclusive astrochemical models.