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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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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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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.
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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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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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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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Introducing chirality in porous organic cages through solid-state interactions.

Emma H Wolpert1,2,3, Kim E Jelfs1

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Achiral molecular cages can form chiral cavities in the solid-state through supramolecular interactions. This study develops a computational method to predict this phenomenon, offering insights for designing chiral materials.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Molecular cages offer versatile applications in separation, storage, and catalysis.
  • Chirality in molecular cages enhances selective separation and introduces novel photophysical properties.
  • Achiral cages can form chiral cavities via solid-state supramolecular interactions.

Purpose of the Study:

  • To develop a computational technique for predicting chiral cavity formation in achiral cages.
  • To investigate the role of supramolecular interactions in inducing chirality in achiral cage systems.
  • To guide the rational design of solid-state materials with targeted chiral properties.

Main Methods:

  • Combination of atomistic calculations and coarse-grained modeling.
  • Predicting crystalline phase behavior of achiral cages.
  • Utilizing dimer pair calculations to inform coarse-grained models for cage packing.

Main Results:

  • A computational method was developed to predict chiral cavity formation in achiral cages.
  • The study focused on the achiral cage B11, demonstrating propeller-like orientations of its arene rings.
  • Supramolecular interactions were shown to drive chirality in achiral cages without chiral guests.

Conclusions:

  • Supramolecular interactions are key to designing chirality in achiral molecular cages.
  • Computational modeling can predict solid-state phase behavior and guide material design.
  • This work is a foundational step towards engineering targeted chiral solid-state properties.