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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...
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...
Chirality in Nature02:30

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. The...
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...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

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...
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...

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Related Experiment Video

Updated: Jun 10, 2026

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

Looking for homochirality in the inter-stellar medium.

G Marloie1, M Lattelais, F Pauzat

  • 1Laboratoire de Chimie Théorique, UPMC Univ. Paris 06, UMR-CNRS 7616, Paris, France.

Interdisciplinary Sciences, Computational Life Sciences
|July 20, 2010
PubMed
Summary
This summary is machine-generated.

Chiral molecules like lactic acid may be detectable in space. Quantum simulations show these molecules are the most stable, making them prime targets for interstellar medium detection. Further lab experiments are recommended.

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A Micropatterning Assay for Measuring Cell Chirality
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A Micropatterning Assay for Measuring Cell Chirality

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Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy
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Multimodal Nonlinear Hyperspectral Chemical Imaging Using Line-Scanning Vibrational Sum-Frequency Generation Microscopy

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Last Updated: Jun 10, 2026

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

A Micropatterning Assay for Measuring Cell Chirality
08:07

A Micropatterning Assay for Measuring Cell Chirality

Published on: March 11, 2022

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:

  • Astrochemistry
  • Quantum Chemistry
  • Astrobiology

Background:

  • Chirality is crucial in biological systems, but the presence of chiral molecules in the interstellar medium (ISM) remains uncertain.
  • The Minimum Energy Principle suggests that the most stable isomer is the most abundant, guiding the search for extraterrestrial molecules.

Purpose of the Study:

  • To investigate the potential detectability of chiral molecules in the ISM.
  • To identify specific chiral molecules that are thermodynamically favored and thus more likely to exist in space.

Main Methods:

  • Utilized quantum simulations based on density functional theory (DFT) to calculate the relative stability of various molecular isomers.
  • Applied the Minimum Energy Principle to predict the abundance of chiral molecules based on their calculated energies.

Main Results:

  • Most chiral isomers within families like acetone, amides, and amino acids are not the most stable species.
  • However, lactic acid, a precursor to alpha-alanine, and the simplest chiral alcohol were found to be the most stable in their respective chemical families.
  • These three identified chiral molecules possess significant dipole moments, enhancing their potential for detection.

Conclusions:

  • Lactic acid and two other specific chiral molecules are predicted to be detectable in the interstellar medium based on their stability.
  • The findings support further laboratory investigations to refine rotational constants for future observational proposals.