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Related Concept Videos

Prochirality02:05

Prochirality

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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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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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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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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Switching the chirality of single adsorbate complexes.

Manfred Parschau1, Daniele Passerone, Karl-Heinz Rieder

  • 1Nanoscale Materials Science, Empa, Swiss Federal Laboratories for Materials Testing and Research, Ueberlandstrasse 129, 8600 Dübendorf, Switzerland.

Angewandte Chemie (International Ed. in English)
|February 12, 2009
PubMed
Summary

Propene molecules on copper surfaces become chiral. Tunneling electrons induce molecular motion and can even convert molecules to their opposite enantiomer, a significant finding in surface chemistry.

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Area of Science:

  • Surface science
  • Physical chemistry
  • Chirality studies

Background:

  • Propene molecules can adsorb onto metal surfaces.
  • Chiral complexes are important in various chemical applications.
  • Electron-induced surface reactions are a key area of research.

Purpose of the Study:

  • To investigate the formation of chiral complexes of propene on a copper surface.
  • To understand the role of tunneling electrons in adsorbate dynamics.
  • To explore enantiomeric conversion induced by electron currents.

Main Methods:

  • Adsorption of propene molecules on a copper (Cu) surface.
  • Utilizing a scanning tunneling microscope (STM) with inelastically scattered electrons.
  • Controlling tunneling currents to influence adsorbate behavior.

Main Results:

  • Propene molecules form chiral complexes when adsorbed on copper.
  • Inelastic electron tunneling induces rotation and diffusion of adsorbed propene.
  • Increased tunneling currents lead to the conversion between enantiomers.

Conclusions:

  • Electron-induced dynamics can control the chirality of adsorbed molecules.
  • STM is a powerful tool for manipulating molecular chirality at surfaces.
  • This work opens avenues for enantioselective surface chemistry.