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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Ladder Diagrams: Redox Equilibria01:30

Ladder Diagrams: Redox Equilibria

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Ladder diagrams are useful tools for understanding redox equilibrium reactions, especially the effects of concentration changes on the electrochemical potential of the reaction. The vertical axis in the redox ladder diagrams represents the electrochemical potential, E. The area of predominance is demarcated using the Nernst equation.
Consider the Fe3+/Fe2+ half-reaction, which has a standard-state potential of +0.771 V. At potentials more positive than +0.771 V, Fe3+ predominates, whereas Fe2+...
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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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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.0K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.1K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Updated: Jun 21, 2025

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
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Switching Product Selectivity in CO2 Electroreduction via Cu-S Bond Length Variation.

Xiaoqian Wei1, Zijian Li2, Haeseong Jang3

  • 1College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China.

Angewandte Chemie (International Ed. in English)
|July 8, 2024
PubMed
Summary

Incorporating antimony into copper sulfide (CuS) switches electrochemical CO2 reduction from formic acid to carbon monoxide. This modification alters the copper-sulfur bond length, enhancing selectivity for desired products.

Keywords:
adsorption characteristicsbond lengthelectrocatalystelectrochemical CO2 reduction reactionselectivity switching

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Catalysis

Background:

  • Controlling selectivity in electrochemical CO2 reduction is vital for sustainable chemical production.
  • Copper sulfide (CuS) is a promising catalyst, but its selectivity needs optimization.

Purpose of the Study:

  • To investigate the effect of antimony (Sb) incorporation into CuS on the selectivity of electrochemical CO2 reduction.
  • To elucidate the relationship between Cu-S bond length and product selectivity.

Main Methods:

  • Synthesis of Sb-doped CuS (Cu3SbS4) and pristine CuS.
  • Electrochemical characterization including Faradaic efficiency measurements.
  • In situ spectroscopy and density functional theory (DFT) calculations.

Main Results:

  • CuS exhibited high selectivity for formic acid (HCOOH) production (72% FE) due to a shorter Cu-S bond (2.24 Å).
  • Cu3SbS4 showed enhanced selectivity for carbon monoxide (CO) production (60% FE) with an elongated Cu-S bond (2.30 Å).
  • DFT calculations revealed weaker *HCOO binding on Cu3SbS4, facilitating CO production.

Conclusions:

  • Antimony incorporation in CuS effectively tunes the Cu-S bond length and local coordination environment.
  • Altered Cu-S bond length in Cu3SbS4 promotes *COOH adsorption, leading to high CO selectivity.
  • This study provides insights into rational catalyst design for selective electrochemical CO2 reduction.