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Related Concept Videos

Chirality02:25

Chirality

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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

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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

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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 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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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.
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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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CSM Software: Continuous Symmetry and Chirality Measures for Quantitative Structural Analysis.

Inbal Tuvi-Arad1, Yaffa Shalit1, Gil Alon2

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This study introduces open-source Python software for calculating continuous symmetry measures (CSMs) and continuous chirality measures (CCMs) in molecules. This tool quantifies molecular structural distortions on a continuous scale, offering nuanced insights beyond binary symmetry assessments.

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Area of Science:

  • Computational Chemistry
  • Molecular Modeling
  • Chemical Physics

Background:

  • Molecular symmetry and chirality are fundamental properties in chemistry.
  • Quantifying these properties often relies on discrete classifications, limiting detailed analysis.
  • Continuous symmetry measures (CSMs) offer a more nuanced approach to assessing molecular geometry.

Purpose of the Study:

  • To present an updated, open-source Python software for calculating CSMs and continuous chirality measures (CCMs).
  • To provide a tool for quantifying molecular structural distortions on a continuous scale.
  • To enable deeper insights into molecular symmetry and chirality across various chemical applications.

Main Methods:

  • Utilizes molecular geometry coordinates as input.
  • Accepts desired cyclic symmetry point groups (Cs, Ci, Cn, Sn).
  • Calculates nearest symmetric structures, symmetry operations, and symmetry/chirality levels (0-100).

Main Results:

  • Provides a comprehensive and updated Python-based open software for CSM and CCM calculations.
  • Outputs detailed symmetry information, including nearest symmetric structures and symmetry element directions.
  • Quantifies symmetry and chirality on a continuous scale, moving beyond binary classifications.

Conclusions:

  • The developed software offers a valuable tool for detailed analysis of molecular symmetry and chirality.
  • CSMs and CCMs provide a continuous measure of structural distortion, enhancing understanding in chemistry.
  • The open-source nature facilitates accessibility and further development in computational chemistry research.