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Related Concept Videos

Prochirality02:05

Prochirality

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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 at Nitrogen, Phosphorus, and Sulfur02:30

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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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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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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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Aromatic Hydrocarbon Anions: Structural Overview01:18

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes
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A Chiral Polycyclic Aromatic Hydrocarbon Monkey Saddle.

Tobias Kirschbaum1, Frank Rominger1, Michael Mastalerz1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Angewandte Chemie (International Ed. in English)
|October 16, 2019
PubMed
Summary

Researchers synthesized a novel monkey saddle polycyclic aromatic hydrocarbon (PAH). This inherently chiral molecule

Keywords:
chiralitycyclooctatetraenemonkey saddlenegative curvaturetruxene

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Polycyclic Aromatic Hydrocarbons (PAHs) are crucial in various scientific fields.
  • Contorted PAHs exhibit unique properties due to their non-planar structures.
  • Developing novel PAH architectures is essential for advancing molecular science.

Purpose of the Study:

  • To synthesize a novel contorted polycyclic aromatic hydrocarbon (PAH) with a unique monkey saddle shape.
  • To characterize the synthesized molecule and investigate its inherent chirality.
  • To elucidate the mechanism of enantiomeric inversion and determine the associated energy barriers.

Main Methods:

  • Three-step synthesis from a truxene precursor.
  • Unambiguous characterization using single-crystal X-ray diffraction.
  • Computational analysis using Density Functional Theory (DFT) methods.
  • Separation of enantiomers via chiral High-Performance Liquid Chromatography (HPLC).
  • Determination of inversion barriers using variable temperature circular dichroism (CD) spectroscopy.

Main Results:

  • Successful synthesis of a monkey saddle-shaped PAH.
  • Confirmation of inherent chirality due to three biaryl axes.
  • DFT calculations indicated a twisting mechanism for enantiomeric inversion.
  • Chiral HPLC successfully separated the enantiomers.
  • Variable temperature CD spectroscopy supported the proposed twisting mechanism for inversion.

Conclusions:

  • A novel chiral monkey saddle PAH was synthesized and characterized.
  • The molecule's chirality arises from its unique contorted structure.
  • Enantiomeric inversion proceeds via a twisting mechanism of peripheral rings, not a planar intermediate.
  • This study provides insights into the synthesis and stereochemical behavior of complex PAHs.