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Related Concept Videos

Chirality02:25

Chirality

24.3K
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...
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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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,...
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Chirality in Nature02:30

Chirality in Nature

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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.
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Prochirality02:05

Prochirality

3.8K
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...
3.8K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.7K
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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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Continuous symmetry and chirality measures: approximate algorithms for large molecular structures.

Gil Alon1, Yuval Ben-Haim2, Inbal Tuvi-Arad3

  • 1Department of Mathematics and Computer Science, The Open University of Israel, Raanana, Israel. gilal@openu.ac.il.

Journal of Cheminformatics
|November 10, 2023
PubMed
Summary

New 3D molecular descriptors quantify structural distortion by measuring deviations from ideal symmetry or chirality. These descriptors offer enhanced accuracy and reliability for analyzing large molecules in various chemical systems.

Keywords:
ChiralityFibonacci latticeHungarian algorithmMolecular descriptorsSupramolecular chemistrySymmetryUnit cells

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Area of Science:

  • Computational Chemistry
  • Structural Chemistry
  • Molecular Modeling

Background:

  • Quantifying molecular structural distortion is crucial for understanding chemical systems.
  • Existing methods for symmetry and chirality measures face challenges with large molecular structures.

Purpose of the Study:

  • To develop novel 3D molecular descriptors for quantifying structural distortion in large molecules.
  • To improve the accuracy, reliability, and structure preservation of symmetry and chirality measures.

Main Methods:

  • Development of 3D geometrical descriptors based on continuous symmetry and chirality measures.
  • Iterative algorithms to efficiently handle permutations and symmetry operations in large structures.
  • Testing algorithms on diverse molecular systems including complexes, fullerenes, and metal-organic frameworks.

Main Results:

  • The new descriptors accurately quantify the deviation from ideal symmetry and chirality.
  • Algorithmic improvements demonstrate increased accuracy, reliability, and structure preservation.
  • Successful application to large and complex molecular structures.

Conclusions:

  • The developed 3D descriptors provide a robust tool for analyzing molecular distortion across various chemical domains.
  • These advancements simplify the application of symmetry and chirality measures in molecular modeling, QSAR, and cheminformatics.
  • The methodology is applicable to organic, inorganic, and biochemical systems.