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

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

22.0K
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...
22.0K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.1K
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...
7.1K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.7K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.7K
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.6K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.6K
Prochirality02:05

Prochirality

5.1K
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...
5.1K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.9K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
11.9K

You might also read

Related Articles

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

Sort by
Same author

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

Science advances·2026
Same author

Individual chemotherapy for patients colorectal cancer based on patient-derived tumor-like cell clusters.

World journal of gastrointestinal surgery·2026
Same author

Regulating π-Stacked Micelle-Like Assembly via Anion Coordination to Achieve Frank-Kasper C15 Phases.

Journal of the American Chemical Society·2026
Same author

Engineering Active Metal and Nonmetal Sites in Porous Structures of Metal-Hydroxide Clusters for Enhanced D<sub>2</sub>/H<sub>2</sub> Uptake and Separation.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2025
Same author

Unveiling the alkyne-π interaction using metal-organic cage compounds.

Communications chemistry·2025
Same author

The Role of Amide-π Stacking in Resolving the DMF-Benzene Miscibility Paradox.

The journal of physical chemistry letters·2025

Related Experiment Video

Updated: Feb 20, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

19.3K

Unlocking spontaneous chiral resolution in silver clusters through steric and anionic control.

Jin Liu1,2,3, Zi-Ang Nan1,2, Qing Li1,2,3

  • 1State Key Laboratory of Structure Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Science Fuzhou Fujian 350002 China nanziang@fjirsm.ac.cn yghuang@fjirsm.ac.cn.

Chemical Science
|February 19, 2026
PubMed
Summary

Researchers designed chiral silver clusters for spontaneous resolution. Ligand design and counterions control homochiral or racemic crystal formation, enabling tunable optical properties.

More Related Videos

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

10.0K
Facet-to-facet Linking of Shape-anisotropic Colloidal Cadmium Chalcogenide Nanostructures
09:12

Facet-to-facet Linking of Shape-anisotropic Colloidal Cadmium Chalcogenide Nanostructures

Published on: August 10, 2017

8.0K

Related Experiment Videos

Last Updated: Feb 20, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

19.3K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

10.0K
Facet-to-facet Linking of Shape-anisotropic Colloidal Cadmium Chalcogenide Nanostructures
09:12

Facet-to-facet Linking of Shape-anisotropic Colloidal Cadmium Chalcogenide Nanostructures

Published on: August 10, 2017

8.0K

Area of Science:

  • Supramolecular Chemistry
  • Crystallography
  • Materials Science

Background:

  • Spontaneous chiral resolution from achiral precursors is challenging to predict.
  • Chirality is crucial for molecular recognition and optical properties.

Purpose of the Study:

  • To develop a rational design strategy for spontaneous chiral resolution.
  • To investigate the influence of ligand sterics and counterions on cluster assembly.
  • To explore the potential of resulting chiral crystals in nonlinear optics.

Main Methods:

  • Synthesis of C3-symmetric tris(2-benzimidazolylmethyl)amine-based trinuclear silver clusters.
  • Controlled variation of ligand substituents and counterions (trifluoromethanesulfonate and methanesulfonate).
  • X-ray diffraction analysis to determine crystal structures and identify chiral self-sorting or social self-sorting.
  • Investigation of anion exchange for reversible switching between chiral and racemic forms.
  • Characterization of optical activity and second-harmonic generation (SHG) responses.

Main Results:

  • Trinuclear silver clusters with sterically demanding ligands and trifluoromethanesulfonate anions yielded homochiral crystals via spontaneous resolution.
  • Clusters with less sterically hindered ligands and trifluoromethanesulfonate resulted in racemic crystals through social self-sorting.
  • Methanesulfonate anions consistently led to social self-sorting, forming racemic crystals.
  • Homochiral structures could be reversibly converted to racemic forms by anion exchange.
  • Chiral crystals exhibited optical activity and SHG responses.

Conclusions:

  • Systematic tuning of intermolecular π⋯π interactions directs chiral self-sorting.
  • Ligand sterics and counterion choice are critical for controlling spontaneous chiral resolution in silver clusters.
  • Controllable switching between chiral and racemic polymorphs is achievable.
  • The developed strategy offers insights for designing spontaneous resolution systems with potential nonlinear optical applications.