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Related Concept Videos

π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

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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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Crystal Field Theory - Octahedral Complexes02:58

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Crystal Field Theory
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Related Experiment Video

Updated: Mar 2, 2026

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Electric-Field-Assisted Anion-π Catalysis.

Masaaki Akamatsu1, Naomi Sakai1, Stefan Matile1

  • 1Department of Organic Chemistry, University of Geneva , 1211 Geneva, Switzerland.

Journal of the American Chemical Society
|May 9, 2017
PubMed
Summary

Electric fields remotely control anion-π catalysis, enhancing reaction rates and selectivity. This electric-field-assisted catalysis shows promise for controlling chemical reactions.

Area of Science:

  • Catalysis
  • Physical Chemistry
  • Materials Science

Background:

  • Anion-π catalysis utilizes catalysts with electron-deficient π systems to interact with anions.
  • Controlling catalytic activity and selectivity remotely is a significant challenge in chemical synthesis.

Purpose of the Study:

  • To investigate the remote control of anion-π catalysis using electric fields.
  • To explore the impact of electric fields on the activity and selectivity of immobilized anion-π catalysts.

Main Methods:

  • Synthesis and immobilization of anion-π catalysts on conductive indium tin oxide surfaces.
  • Studying the addition reaction of malonic acid half thioesters to enolate acceptors under varying electric fields.
  • Investigating the effect of nitrate addition on catalyst responsiveness to electric fields.

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Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F−
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Main Results:

  • Anion-π catalyst activity and selectivity were modulated by applied electric fields.
  • A >100-fold rate enhancement was observed for a disfavored reaction pathway.
  • Selectivity of transition-state recognition improved by up to -14.8 kJ mol-1.
  • Nitrate addition (IC50 = 2.2 mM) abolished electric field responsiveness.

Conclusions:

  • Electric fields can polarize the π-acidic surface of anion-π catalysts, enhancing recognition of anionic intermediates and transition states.
  • This demonstrates the existence and practical relevance of electric-field-assisted anion-π catalysis.
  • The findings open new avenues for remote control of catalytic processes.