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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Radical Formation: Homolysis00:54

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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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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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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A Uranyl Peroxide Dimer in the Gas Phase.

Phuong D Dau1, Phuong V Dau1, Linfeng Rao1

  • 1Chemical Sciences Division, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.

Inorganic Chemistry
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Summary

The study synthesized a gas-phase uranyl peroxide dimer and investigated its reactions. Gas-phase computations reveal the uranyl-peroxide-uranyl unit is inherently planar, requiring minimal energy to form bent structures.

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Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Uranyl peroxide complexes are crucial in nuclear fuel reprocessing and environmental remediation.
  • Understanding the structural dynamics of uranyl peroxide species is key to controlling their reactivity and formation.

Purpose of the Study:

  • To synthesize and characterize a gas-phase uranyl peroxide dimer.
  • To investigate the reaction pathways of the dimer, including O atom elimination and hydrolysis.
  • To computationally evaluate the structural stability and bending energies of uranyl peroxide complexes.

Main Methods:

  • Electrospray ionization (ESI) for synthesis of the uranyl peroxide dimer.
  • Collision-induced dissociation (CID) to study fragmentation pathways.
  • Density functional theory (DFT) for computational energy and structure analysis.

Main Results:

  • The gas-phase uranyl peroxide dimer [(UO2)2(O2)(L)2]2+ was successfully synthesized.
  • Collision-induced dissociation revealed endothermic O atom elimination, followed by exothermic hydrolysis.
  • DFT calculations supported experimental observations and indicated that the uranyl-peroxide-uranyl unit is intrinsically planar.

Conclusions:

  • The uranyl peroxide moiety exhibits inherent stability in the gas phase.
  • Minor energy input is sufficient to induce bending in uranyl peroxide complexes, explaining bent structures in condensed phases.
  • Gas-phase studies provide valuable insights into the formation of condensed-phase uranyl peroxides like studtite.