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Related Concept Videos

Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

Oxidation–Reduction Reactions
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
Electron Transport Chain: Complex III and IV01:43

Electron Transport Chain: Complex III and IV

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...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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 property is crucial in...
Redox Reactions01:24

Redox Reactions

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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Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry
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Four-electron oxygen reduction by tetrathiafulvalene.

Astrid J Olaya1, Peiyu Ge, Jérôme F Gonthier

  • 1Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland.

Journal of the American Chemical Society
|July 1, 2011
PubMed
Summary

Tetrathiafulvalene (TTF) facilitates the four-electron reduction of oxygen to water in an acidic organic solvent. A helical tetramer assembly of protonated and neutral TTF molecules is proposed to mediate this crucial electrochemical reaction.

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Area of Science:

  • Electrochemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Oxygen reduction is a critical process in energy conversion.
  • Tetrathiafulvalene (TTF) is a redox-active organic molecule with potential applications in catalysis.
  • Understanding the mechanism of oxygen reduction by organic mediators is essential for developing new electrochemical systems.

Purpose of the Study:

  • To investigate the four-electron reduction of oxygen mediated by tetrathiafulvalene (TTF).
  • To elucidate the reaction mechanism and identify key intermediates.
  • To explore the potential of TTF in facilitating oxygen reduction in non-aqueous and interfacial environments.

Main Methods:

  • Spectroscopy (UV-Vis, IR)
  • Ion transfer voltammetry
  • Electrochemical measurements
  • Electronic structure computations (DFT)
  • (1)H NMR spectroscopy

Main Results:

  • The four-electron reduction of oxygen by TTF was observed in acidified 1,2-dichloroethane and at the water/organic interface.
  • Spectroscopic and electrochemical data suggest a mechanism involving rapid TTF protonation followed by oxygen reduction.
  • Electronic structure calculations revealed the formation of a helical tetramer ([TTF(4)H(2)](2+)) of protonated and neutral TTF molecules.
  • Water production was confirmed by (1)H NMR analysis.

Conclusions:

  • Tetrathiafulvalene acts as an effective mediator for the four-electron reduction of oxygen.
  • A helical tetramer intermediate plays a crucial role in delivering electrons for oxygen reduction.
  • The findings provide insights into the electrochemical behavior of TTF and its potential in catalytic oxygen reduction.