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

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.0K
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,...
9.0K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

11.8K
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...
11.8K
Prochirality02:05

Prochirality

3.8K
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...
3.8K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.8K
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...
5.8K
Stereoisomers02:32

Stereoisomers

13.0K
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...
13.0K
Chirality02:25

Chirality

24.4K
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...
24.4K

You might also read

Related Articles

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

Sort by
Same author

The Selective Routing of Plasmonic Interface Charge Transfer in Enhanced Raman Spectroscopy or Chemical Reaction.

Journal of the American Chemical Society·2026
Same author

Enhanced glymphatic CSF tracer influx during α2-adrenergic agonist anesthesia is independent of tracer injection duration.

bioRxiv : the preprint server for biology·2026
Same author

Electrothermal vacuum sublimation drying of graphene aerogels for high-temperature synthesis.

Nature communications·2026
Same author

AirNet: A Deep Learning-Driven Auto Baseline Correction Algorithm Balancing Global Smoothness and Local Fidelity.

Analytical chemistry·2026
Same author

Hydrogen-Bond Network-Activated O<sub>2</sub> in ChCl-Based Deep Eutectic Solvent Lowers the Overpotential of Oxygen Reduction Reaction on Carbon Electrode.

ChemSusChem·2026
Same author

Sol-gel interconvertible 62-component dodecahedra assembled via amide-Ï€-assisted anion-coordination nanoarchitectonics.

Science advances·2026

Related Experiment Video

Updated: Jul 20, 2025

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

10.4K

Chiral Molecular Cage with Tunable Stereoinversion Barriers.

Wen-Bin Gao1, Zhihao Li1, Tianyi Tong1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM) and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

Journal of the American Chemical Society
|August 1, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a dynamic face-rotating tetrahedron (FRT) cage. Its chirality can be controlled by fluoride anions and enantiopure phenylethanol, offering new insights into dynamic stereochemistry.

More Related Videos

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
09:44

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

12.3K
Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

8.2K

Related Experiment Videos

Last Updated: Jul 20, 2025

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

10.4K
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
09:44

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

12.3K
Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

8.2K

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Stereochemistry

Background:

  • Controlling dynamic chirality in rapidly interconverting enantiomers is a significant challenge, especially at the supramolecular level.
  • Understanding chiral symmetry breaking and homochirality is crucial for advancing stereochemical control.

Purpose of the Study:

  • To synthesize a novel face-rotating tetrahedron (FRT) molecular cage capable of dynamic stereomutation.
  • To investigate methods for in situ regulation of the racemization barrier and induction of chirality in the FRT system.

Main Methods:

  • Synthesis of a face-rotating tetrahedron (FRT) using tridurylborane facial units.
  • Chiral resolution of the FRT.
  • In situ regulation of racemization barrier via fluoride anion binding.
  • Chirality induction using enantiopure phenylethanol.

Main Results:

  • The synthesized FRT exhibits stereomutations between enantiomeric propeller-like conformations.
  • The racemization barrier of the enantiopure FRT is successfully regulated by reversible fluoride anion binding.
  • Enantiopure phenylethanol addition effectively induces chirality in the FRT by preferential binding to one enantiomer.

Conclusions:

  • This study introduces a new paradigm for controlling dynamic chirality in supramolecular systems.
  • The developed FRT system demonstrates tunable stereochemistry with potential applications in asymmetric synthesis and dynamic stereochemistry.