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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.6K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
2.6K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.9K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.9K
Radical Autoxidation01:20

Radical Autoxidation

3.3K
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
3.3K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.6K
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.
7.6K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.3K
Temperature Dependence on Reaction Rate02:55

Temperature Dependence on Reaction Rate

90.1K
The Collision Theory
Atoms, molecules, or ions must collide before they can react with each other. Atoms must be close together to form chemical bonds. This premise is the basis for a theory that explains many observations regarding chemical kinetics, including factors affecting reaction rates.
The collision theory is based on the postulates that (i) the reaction rate is proportional to the rate of reactant collisions, (ii) the reacting species collide in an orientation allowing contact between...
90.1K

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ダイオキシゲン:この三連鎖を 動的持続性のあるものにするのは何か?

Weston Thatcher Borden1, Roald Hoffmann2, Thijs Stuyver3,4

  • 1Department of Chemistry and the Center for Advanced Scientific Computing and Modeling, University of North Texas , 1155 Union Circle, #305070, Denton, Texas 76203-5017, United States.

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まとめ
この要約は機械生成です。

三重分子酸素 (O2) は有意義な共鳴安定性を有しており,その豊富な存在と有酸素生命における役割を説明する. しかし,この安定化は,特定の酸素反応を可能にする弱いO-Oシグマ結合と対照的です.

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Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase
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Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
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科学分野:

  • 物理化学
  • 量子化学について
  • 生物化学

背景:

  • 三重分子酸素 (O2) は有酸素生命にとって不可欠ですが,ユニークな反応パターンを表しています.
  • O2の電子構造と安定化を理解することは,生物系におけるその豊富さと役割を説明する鍵です.
  • 以前の研究では O2 の熱力学特性と反応機構を調査した.

研究 の 目的:

  • 三重 O2 の共振安定化エネルギーを定量化する.
  • 分子軌道 (MO) とバレンスの結合 (VB) の理論を用いてこの安定化の起源を解明する.
  • O2の水素原子抽象化と小分子化反応の観測された熱力学的不利性との共振安定化を相関させる.

主な方法:

  • 形成熱とエンタルピーの実験的決定.
  • G4 量子化学計算について
  • 分子軌道 (MO) とバレンスの結合 (VB) の理論の枠組み内の分析.

主要な成果:

  • 実験とG4計算の結果は,2つのヒドロキシルラジカルと比較してトリプルO2の共振安定化エネルギーが約100kcal/molであることを示しています.
  • この大きな安定エネルギーは,MOとVB理論によって説明されるように,O2のペア化されていない電子の電子構成から生じる.
  • 水素原子の抽象化とオリゴメリゼーションの熱力学的不利性は,この有意な共振安定化に直接起因する.

結論:

  • 三重体O2の実質的な共鳴安定化が,その生態系における持続性を説明し,有酸素生命を支えている.
  • πシステムの安定化にもかかわらず,O−O σ結合の固有の弱さにより,O2は結合分裂を含む反応に敏感になる.
  • 共振安定化と σ結合の弱さの相互作用は,分子酸素の全体的な反応性プロファイルを支配する.