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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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An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0,...
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The Electron Spin as a Chiral Reagent.

Tzuriel S Metzger1, Suryakant Mishra2, Brian P Bloom3

  • 1Applied Physics Department and the Center for Nano-Science and Nano-Technology, The Hebrew University of Jerusalem, Jerusalem, 91904, Israel.

Angewandte Chemie (International Ed. in English)
|October 18, 2019
PubMed
Summary

Electron spin can now induce enantioselective reactions, replacing traditional chiral reagents. Spin-polarized electrons provide the necessary chiral bias for these novel chemical transformations.

Keywords:
chiral-induced spin selectivitychiralityelectrochemistryenantioselectivityspin

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Area of Science:

  • Chemistry
  • Physics
  • Materials Science

Background:

  • Enantioselective reactions are crucial in synthesizing chiral molecules, typically relying on enantiopure reagents.
  • Developing alternative methods to control enantioselectivity is essential for advancing chemical synthesis.

Purpose of the Study:

  • To demonstrate that electron spin polarization can induce enantioselective reactions.
  • To explore the replacement of conventional chiral reagents with spin-polarized electrons.
  • To present examples of enantioselective chemistry driven by electron spin polarization.

Main Methods:

  • Investigating the enantioselective association of chiral molecules with spin-polarized self-assembled monolayers.
  • Examining enantiospecific electrochemical reduction and oxidation reactions driven by electron helicity.
  • Analyzing the role of spin polarization at the substrate-molecule interface.

Main Results:

  • Electron spin polarization successfully induced enantioselective reactions.
  • Spin-polarized electrons replaced conventional chiral reagents in driving enantioselectivity.
  • Demonstrated enantioselective association and enantiospecific electrochemical reactions.
  • Confirmed that enantioselectivity originates from spin polarization crossing the interface, not molecule-electrode interactions.

Conclusions:

  • Electron spin polarization offers a new mechanism for achieving enantioselective chemistry.
  • The direction of electron spin polarization dictates the handedness of enantioselectivity.
  • This approach provides a novel pathway for controlling chiral outcomes in chemical reactions.