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Related Concept Videos

Chirality02:25

Chirality

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...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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...
Fischer Projections02:18

Fischer Projections

Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
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,...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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...
Prochirality02:05

Prochirality

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...

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Related Experiment Video

Updated: Jul 9, 2026

Spatial Separation of Molecular Conformers and Clusters
10:37

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

Chiral separation: mechanism modeling in two-dimensional systems.

Irina Paci1, Igal Szleifer, Mark A Ratner

  • 1Department of Chemistry and Materials Research Center, Northwestern University, Evanston, Illinois 60208, USA. ipaci@chem.northwestern.edu

Journal of the American Chemical Society
|March 7, 2007
PubMed
Summary
This summary is machine-generated.

An achiral surface can induce chiral separation in racemates by restricting molecular configurations. Controlling interactions promotes self-assembly into homochiral clusters, overcoming bulk racemic limitations.

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Last Updated: Jul 9, 2026

Spatial Separation of Molecular Conformers and Clusters
10:37

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

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

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:

  • Physical Chemistry
  • Surface Science
  • Chirality Studies

Background:

  • Fluid phase separation of racemates is challenging due to weak chiral intermolecular interactions.
  • Surfaces can alter molecular interactions, potentially enabling chiral separation.
  • Understanding surface-induced chiral symmetry breaking is crucial for separation technologies.

Purpose of the Study:

  • Investigate chiral symmetry breaking in racemates induced by an achiral surface.
  • Explore the role of molecular geometry and energetics in surface-confined chiral separations.
  • Determine conditions for achieving homochiral cluster formation.

Main Methods:

  • Utilized a parallel tempering Monte Carlo algorithm with temperature domain tempering.
  • Simulated a two-dimensional system of chiral molecules interacting with an achiral surface.
  • Analyzed the balance between electrostatic and steric interactions.

Main Results:

  • Achiral surfaces can promote chiral segregation in racemates by restricting configurational space.
  • Controlling electrostatic and steric interactions directs assembly into homochiral micellar clusters.
  • Even with complex molecules favoring heterochiral pairs, multibody and entropic effects can still yield homochiral micelles.

Conclusions:

  • Surface confinement is a viable strategy for achieving chiral separations of racemates.
  • Molecular shape, electrostatic, and steric interactions collectively govern surface-induced chiral assembly.
  • Predicting racemate segregation requires considering multibody and entropic effects beyond pairwise interactions.