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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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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines.
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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.
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Chirality in Nature02:30

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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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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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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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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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From Helices to Crystals: Multiscale Representation of Chirality in Double-Helix Structures.

Chong-Yang Li1, Han Xu1, Pei-Ming Cheng1

  • 1Collaborative Innovation Center of Chemistry for Energy Materials, State Key Laboratory of Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.

Journal of the American Chemical Society
|October 2, 2023
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Summary

Researchers discovered a rare phenomenon of chirality transfer from atoms to double-helical structures and chiral crystals. This finding reveals potential for novel lanthanide-based magneto-optical materials.

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Area of Science:

  • Materials Science
  • Crystallography
  • Organic Chemistry

Background:

  • Chiral crystals exhibit unique polarization rotation properties.
  • The formation mechanism of large-scale chiral crystal structures is not fully understood.

Purpose of the Study:

  • To investigate the multitransfer and expression of chirality across different scales.
  • To elucidate the mechanism behind chiral crystal formation.
  • To explore the magneto-optical properties of lanthanide-based chiral helical structures.

Main Methods:

  • Chiral crystal synthesis and characterization.
  • Crystal face analysis and theoretical morphology.
  • Magnetic Circular Dichroism (MCD) spectroscopy.

Main Results:

  • Demonstrated chirality transfer from chiral carbon atoms to double-helical structures and macroscopic crystals.
  • Identified intrinsic symmetrical distribution and acquired growth of crystal faces as key factors in chiral crystal formation.
  • Observed a strong magneto-optical response in lanthanide-based chiral helical structures, with the CD signal reversible by an external magnetic field.

Conclusions:

  • The study reveals a comprehensive mechanism for chiral crystal formation driven by amino acid-derived amide groups.
  • Lanthanide-based chiral helical structures show significant potential as advanced magneto-optical materials.