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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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 factors, steric factors also account...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radical Formation: Overview01:03

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the latter, also known...
Radical Formation: Addition00:47

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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.
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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 carbon–halogen...

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Updated: May 16, 2026

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

機械的結合によって誘発される根の安定化.

Hao Li1, Zhixue Zhu, Albert C Fahrenbach

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States.

Journal of the American Chemical Society
|November 21, 2012
PubMed
まとめ
この要約は機械生成です。

研究者らは,安定した根性カチオンを持つ新しい [2] ロタキサンを合成した. これらの分子機械は,調節可能なシャトルバリアと,パラマグネティックな材料や導電性デバイスの潜在能力を示しています.

さらに関連する動画

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

関連する実験動画

Last Updated: May 16, 2026

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

科学分野:

  • 超分子化学 超分子化学
  • マテリアルサイエンス 材料科学
  • 有機化学 オーガニック・ケミストリー

背景:

  • ロタキサン (Rotaxanes) は,分子装置における潜在的応用がある機械的に相互に絡み合っている分子である.
  • 安定したラジカルカチオンは,先進的な材料の重要な構成要素です.
  • 4,4'-ビピリジニウム (BIPY(2+)) 単位は,リドックス活性系における一般的な構成要素である.

研究 の 目的:

  • 4,4'-ビピリジニウム (BIPY(2+)) のダンベル部品に,サイクロビス (((パラクアット-p-フェニレン)) (CBPQT (((4+)) と異なるオリゴメチレン鎖長を持つ同類の [2]ロタキサンを合成する.
  • 結果として生じるBIPY (((•+) 基離子の電気化学的性質と安定性を調査する.
  • 分子構造とリングシャトルのダイナミクスの関係を探求する.

主な方法:

  • ラジカルテンプレーションと無銅アジド・アルキンサイクル添加反応を用いた合成.
  • サイクルボルトメトリー,UV/visスペクトロスコーピー,質量スペクトロメトリー,および1H NMRスペクトロスコーピーによる特徴付け.

主要な成果:

  • 酸化に耐性のある安定したBIPY (((•+) 基離子を持つ一連の[2]ロタキサンを成功して合成した.
  • 酸化形態における強化されたクーロンビック反発の観察,基底状態のココンフォーメーションの不安定化.
  • 最小の[2]ロタキサンは,環境条件下ではモノラジカルとして存在します.
  • 鎖の長さの増加に伴い,リングシャトルの活性化エネルギーバリアの線形増加.

結論:

  • 高度安定したBIPY ((•+) 基離子を生成するための新しい方法が開発されました.
  • 合成された[2]ロタキサンは,潜在的な応用のために調節可能な分子ダイナミクスを提供します.
  • これらの発見は,パラマグネティック材料と伝導性分子電子機器の構築の道を開く.