Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

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...
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...
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,...
Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

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 different...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Asymmetric synthesis of alkyl fluorides <i>via</i> biocatalytic reduction of α-fluoroenones and α-fluoroenoates.

Green chemistry : an international journal and green chemistry resource : GC·2026
Same author

Tuning Decomposition Temperature: A Structural Study of Ligand Directed Bonding and Fluxionality.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

The Influence of Disulfide, Thioacetal and Lanthionine-Bridges on the Conformation of a Macrocyclic Peptide.

Chemistry (Weinheim an der Bergstrasse, Germany)·2024
Same author

Competitive Intramolecular Hydrogen Bonding: Offering Molecules a Choice.

ChemPlusChem·2024
Same author

Use of pyridazinediones for tuneable and reversible covalent cysteine modification applied to peptides, proteins and hydrogels.

Chemical science·2023
Same author

EGFR-targeted semiconducting polymer nanoparticles for photoacoustic imaging.

Bioorganic & medicinal chemistry·2023

Related Experiment Video

Updated: May 21, 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

Diastereomer configurations from joint experimental-computational analysis.

Abil E Aliev1, Zakirin A Mia, Mathilde J M Busson

  • 1Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK. A.E.Aliev@ucl.ac.uk

The Journal of Organic Chemistry
|June 28, 2012
PubMed
Summary

This study demonstrates a computational method combining nuclear magnetic resonance (NMR) spectroscopy with molecular simulations to determine diastereomer configurations. The approach accurately resolves stereochemistry by matching experimental and calculated NMR parameters.

More Related Videos

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
14:55

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

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

Related Experiment Videos

Last Updated: May 21, 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

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
14:55

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

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

Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • Determining stereochemistry, specifically diastereomer configurations, is crucial in organic chemistry.
  • Traditional methods can be labor-intensive and may not provide full structural insights.

Purpose of the Study:

  • To demonstrate a combined computational and experimental approach for accurate diastereomer configuration determination.
  • To validate the method using four diastereomers of a trisubstituted epoxide.

Main Methods:

  • Utilizing nuclear magnetic resonance (NMR) spectroscopy, relaxed grid search (RGS), molecular dynamics (MD) simulations, and quantum mechanical (QM) calculations.
  • Identifying conformer populations via RGS and MD, followed by QM geometry optimization and energy calculations.
  • Calculating averaged NMR parameters (chemical shifts, J couplings, NOEs) using QM and matching them with experimental data.

Main Results:

  • The combined approach successfully determined the configurations of the four diastereomers.
  • Agreement of three different NMR parameters (chemical shifts, J couplings, NOEs) confirmed the resolved configurations.
  • The method provided a full structural and dynamics characterization of each diastereomer.

Conclusions:

  • The integration of NMR spectroscopy with RGS, MD, and QM calculations is a powerful tool for diastereomer configuration determination.
  • This method offers a comprehensive structural and dynamic understanding beyond just configuration assignment.
  • The validated approach enhances stereochemical analysis in complex organic molecules.