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Related Concept Videos

Oxidation of Phenols to Quinones01:17

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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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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Electron Transport Chain: Complex III and IV01:43

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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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Preparation of Diols and Pinacol Rearrangement01:57

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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The Electron Transport Chain01:30

The Electron Transport Chain

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The electron transport chain or oxidative phosphorylation is an exothermic process in which free energy released during electron transfer reactions is coupled to ATP synthesis. This process is a significant source of energy in aerobic cells, and therefore inhibitors of the electron transport chain can be detrimental to the cell's metabolic processes.
Inhibitors of the electron transport chain
Rotenone, a widely used pesticide, prevents electron transfer from Fe-S cluster to ubiquinone or Q...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Diphenoquinones Redux.

Sébastien Néron1, Mathieu Morency1, Liguo Chen1

  • 1Département de Chimie, Université de Montréal, Montréal, Québec H2V 0B3, Canada.

The Journal of Organic Chemistry
|June 6, 2022
PubMed
Summary
This summary is machine-generated.

4,4'-Diphenoquinones, a class of organic compounds, show promise for green batteries due to their reversible reductions. Their unique structure and electrochemical properties make them suitable for advanced carbon-based electrochemical devices.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Benzoquinones are explored for green carbon-based batteries due to reversible reductions.
  • 4,4'-Diphenoquinones possess extended quinonoid structures and are a less-studied compound class.
  • These compounds feature nearly planar cores with a long interannular C═C bond.

Purpose of the Study:

  • To explore the synthesis, characterization, and electrochemical properties of 4,4'-diphenoquinones.
  • To assess their potential as active materials in electrochemical devices.
  • To establish diphenoquinones within mainstream chemistry for redox-active applications.

Main Methods:

  • Synthesis, isolation, crystallization, and full characterization of diphenoquinones.
  • Experimental and computational approaches to determine structural and electronic properties.
  • Electrochemical studies in solution and solid states.

Main Results:

  • 4,4'-Diphenoquinones exhibit nearly planar cores and unique solid-state associations (chains/sheets via C-H···O interactions).
  • Unsubstituted derivatives show reactivity towards hydration and dimerization.
  • Diphenoquinones demonstrate rapid, reversible reductions at higher potentials than analogous benzoquinones.

Conclusions:

  • Diphenoquinones are a versatile class of compounds with tunable electrochemical properties.
  • Their unique structural and electronic characteristics are suitable for developing redox-active materials.
  • These findings provide a foundation for utilizing diphenoquinones in green carbon-based electrochemical devices.