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Redox Reactions01:27

Redox Reactions

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Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
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Redox Reactions01:24

Redox Reactions

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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Electron Transport Chain: Complex III and IV01:43

Electron Transport Chain: Complex III and IV

9.8K
During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

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Oxidation–Reduction Reactions
78.9K
Extraction: Advanced Methods00:56

Extraction: Advanced Methods

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Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is...
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Related Experiment Video

Updated: Apr 10, 2026

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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[CuO](+) and [CuOH](2+) complexes: intermediates in oxidation catalysis?

Nicole Gagnon1, William B Tolman1

  • 1Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota, 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.

Accounts of Chemical Research
|June 16, 2015
PubMed
Summary

Researchers explored copper intermediates for C-H bond oxidation catalysis. They synthesized a [CuOH](2+) complex that rapidly abstracts hydrogen atoms, even from strong C-H bonds, suggesting its role in catalytic mechanisms.

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Area of Science:

  • Inorganic Chemistry
  • Catalysis
  • Oxidation Mechanisms

Background:

  • Characterizing monocopper intermediates is crucial for understanding oxidation catalysis and designing efficient catalysts.
  • Initial Cu(I)/O2 adducts are sluggish with strong C-H bonds, suggesting more reactive species like [CuO](+) or [CuOH](2+) may form.
  • Gas-phase studies of [CuO](+) offer insights, but solution/solid-state data for [CuO](+) and [CuOH](2+) complexes are limited.

Purpose of the Study:

  • To synthesize and characterize discrete [CuO](+) or [CuOH](2+) complexes in solution or solid state.
  • To investigate reaction pathways that implicate [CuO](+) intermediates using Cu(I)-α-ketocarboxylate and N-oxide complexes.
  • To synthesize and characterize [CuOH](2+) complexes and evaluate their reactivity towards strong C-H bonds.

Main Methods:

  • Explored reactions of O2 with Cu(I)-α-ketocarboxylate complexes.
  • Investigated reactions of N-oxides with Cu(I) complexes to form [CuO](+) species.
  • Synthesized [LCu(II)OH](-) complexes using pyridine-dicarboxamide ligands, followed by one-electron oxidation to form [CuOH](2+) complexes.
  • Determined O-H bond dissociation enthalpy (BDE) via pKa and reduction potential measurements.
  • Studied hydrogen atom abstraction (HAT) kinetics with dihydroanthracene (DHA) and other substrates with varying C-H BDEs.

Main Results:

  • Indirect evidence for [CuO](+) intermediates was obtained, dependent on ligand choice.
  • Successfully synthesized and characterized [CuOH](2+) complexes in solution.
  • Observed rapid HAT from DHA by the [CuOH](2+) complex, with an O-H BDE of ~90 kcal/mol.
  • Demonstrated reactivity towards substrates with C-H bond strengths as high as 99 kcal/mol.
  • Established a linear correlation between log k and C-H BDE, supporting HAT mechanisms.

Conclusions:

  • The [CuOH](2+) core is a viable intermediate in oxidation catalysis, potentially more accessible than [CuO](+).
  • The high O-H BDE of the [CuOH](2+) complex, coupled with hydroxide basicity, facilitates rapid HAT.
  • These findings provide crucial evidence for the role of [CuOH](2+) in catalytic C-H bond oxidation.
  • The study suggests considering [CuOH](2+) as an alternative intermediate in proposed oxidation mechanisms.