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Chirality at Nitrogen, Phosphorus, and Sulfur

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...

Chirality

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...

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

Molecules with Multiple Chiral Centers

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...

Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Prochirality

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: Feb 19, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Chiral Imprinting in the Gas Phase.

David W Pratt¹, Brooks H Pate²

¹University of Vermont, Department of Chemistry, Discovery Building, 82 University Place, Burlington, 05405, USA.

Angewandte Chemie (International Ed. in English)

|November 9, 2017

Summary

Scientists can now control molecular handedness. Using precise microwave pulses, they successfully altered the proportions of specific enantiomers in a large gas-phase molecule, a breakthrough in chiral chemistry.

Keywords:

chiral recognition enantiomer enrichment gas phase chemistry rotational spectroscopy terpenes

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Last Updated: Feb 19, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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Published on: August 18, 2017

A Micropatterning Assay for Measuring Cell Chirality

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Published on: March 11, 2022

Spatial Separation of Molecular Conformers and Clusters

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

Area of Science:

Chirality and molecular symmetry
Quantum control of molecular populations
Gas-phase spectroscopy

Background:

Enantiomers are non-superimposable mirror-image molecules with identical physical properties.
Controlling enantiomeric populations is crucial for pharmaceuticals and materials science.
Previous methods for enantiomeric separation or enrichment were often complex or inefficient.

Purpose of the Study:

To demonstrate the selective manipulation of enantiomeric populations in large gas-phase molecules.
To explore the use of resonant microwave fields for controlling molecular chirality.
To establish a novel method for enantiomeric enhancement.

Main Methods:

Application of phase- and polarization-controlled microwave pulse sequences.
Targeting specific enantiomers of a chiral terpene in the gas phase.
Monitoring changes in relative enantiomeric populations.

Main Results:

Successful enhancement of one enantiomer's population over the other.
Demonstration of precise control over molecular enantiomeric ratios.
Validation of microwave-driven population transfer for chiral molecules.

Conclusions:

Resonant microwave fields offer a viable pathway for controlling enantiomeric composition.
This technique provides a new tool for enantioselective synthesis and separation.
The findings open avenues for manipulating molecular chirality with high precision.