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

Chirality in Nature02:30

Chirality in Nature

13.5K
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.
13.5K
Prochirality02:05

Prochirality

4.0K
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...
4.0K
Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

1.9K
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
1.9K
Chirality02:25

Chirality

23.2K
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...
23.2K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.4K
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...
5.4K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.8K
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...
9.8K

You might also read

Related Articles

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

Sort by
Same author

Threonine Phosphorylation Is a Bioreversible Surrogate of Proline Hydroxylation in a Collagen Triple Helix.

Journal of the American Chemical Society·2026
Same author

Reductive Methylation: An Alternative to Lysine → Arginine Mutagenesis.

Journal of peptide science : an official publication of the European Peptide Society·2026
Same author

Backbone Nitrogen Substitution Probes the Role of Glycine Residues at GxxxG Interfaces in Transmembrane Helices.

Biochemistry·2026
Same author

α-Alkylated α-amino acids reduce the aggregation of unfolded peptides.

RSC advances·2026
Same author

Anti-CRISPR-mediated continuous directed evolution of CRISPR-Cas9 in human cells.

Proceedings of the National Academy of Sciences of the United States of America·2026
Same author

Mutational Scanning of α-Synuclein using a Clickable Protein Tag Reveals Determinants of Membrane-Induced Aggregation.

bioRxiv : the preprint server for biology·2026

Related Experiment Video

Updated: Apr 28, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K

n→π* interactions engender chirality in carbonyl groups.

Amit Choudhary1, Robert W Newberry, Ronald T Raines

  • 1Graduate Program in Biophysics and Departments of ‡Chemistry and §Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

Organic Letters
|June 14, 2014
PubMed
Summary
This summary is machine-generated.

Electron delocalization via n→π* interactions can induce chirality in planar carbonyl groups. This subtle electronic effect has significant stereochemical consequences, as demonstrated in crystallographic studies.

More Related Videos

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

9.6K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.0K

Related Experiment Videos

Last Updated: Apr 28, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K
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

9.6K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.0K

Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Crystallography

Background:

  • n→π* interactions involve electron delocalization from a donor group's electron pair (n) into a carbonyl group's antibonding orbital (π*).
  • These interactions are typically subtle and their stereochemical implications are not fully understood.

Purpose of the Study:

  • To investigate the stereochemical consequences of n→π* interactions.
  • To determine if n→π* interactions can induce chirality in prochiral carbonyl groups.

Main Methods:

  • Crystallographic analysis of five pairs of diastereoisomers.
  • Analysis of electron delocalization patterns.

Main Results:

  • Crystallographic data confirmed the presence and influence of n→π* interactions.
  • n→π* interactions were shown to induce chirality in otherwise planar, prochiral carbonyl groups.
  • The electron delocalization associated with n→π* interactions has measurable stereochemical effects.

Conclusions:

  • Subtle electron delocalization through n→π* interactions can lead to significant stereochemical outcomes.
  • n→π* interactions are a key factor in controlling chirality in certain molecular systems.
  • This finding has implications for understanding and designing chiral molecules.