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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.3K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
5.3K
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 Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.6K
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: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.7K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.7K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.3K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.3K

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Updated: Mar 7, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

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サイズのマッチングによる根元多様性

Mark C Lipke1, Tao Cheng2, Yilei Wu1

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

Journal of the American Chemical Society
|February 8, 2017
PubMed
まとめ
この要約は機械生成です。

研究者らは,新しい分子正方形ホストを開発し,特定のダイラジカルサイクロファンのゲストを,ラジカルペアリングの相互作用によって選択的に結合させました. これは安定した四根基複合体を作り,超分子化学における分子認識を進める.

さらに関連する動画

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Following the Dynamics of Structural Variants in Experimentally Evolved Populations
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Following the Dynamics of Structural Variants in Experimentally Evolved Populations

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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Published on: April 15, 2013

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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科学分野:

  • 超分子化学
  • 材料科学
  • 有機化学

背景:

  • メチルバイオゲンラジカルカチオン (MV+•) のような持続的なπ-ラジカルは,弱いラジカル-ラジカル相互作用を示す.
  • これらの相互作用は,安定した宿主-ゲスト複合体の形成を可能にする,超分子化学の鍵です.
  • 前回の研究では,MVとサイクロファンの宿主[サイクロビス (paraquat-p-phenylene) ] (CBPQT) の間で強い複合体が確立された.

研究 の 目的:

  • ラジカルペアリングベースの分子認識を,より大きな正方形のダイラジカルホストに拡張するために, [cyclobis (((paraquat-4,4'-biphenylene) ] (MS)
  • MS2(+•)を持つイソメアジラジカルサイクロファンの結合を評価する.
  • 結果のテトララジカル複合体を特徴付け,その安定性を支配する要因を理解する.

主な方法:

  • 複合形成と結合親和度を監視するためのUV-Vis-NIRスペクトロスコーピー.
  • 熱力学的パラメータを決定するためのタイトリング実験と可変温度スペクトロスコーピー (UV-Vis-NIR, EPR).
  • 構造分析のための単結晶X線微分と密度関数理論 (DFT) の計算.
  • 複合体の電子特性を検知するサイクル電圧測定法

主要な成果:

  • MS2(+•) は選択的にメタキシリレン関連ダイラジカルサイクロファン (m-CBPQT2(+•) を結合し,テトララジカル複合体 [MSm-CBPQT]4(+•) を形成する.
  • 結合は,好ましいエンタルピー変化によって引き起こされるが,エントロピックペナルティによって相殺され,より小さなシステムと比較できるアソシエーション定数 (Ka = (1.12 ± 0.08) × 105 M-1) が得られる.
  • 構造分析により,m-CBPQT2(+•)はMS2(+•)にとって理想的なサイズであり,複合体は結晶構造における典型的な拡張根配列を破壊する.
  • サイクリック・ボルトメトリーは, 複合体内の基質状態の安定化を確認します.

結論:

  • この研究は,より大きな正方形の宿主に対する 根幹配列分子認識の拡張を成功裏に実証した.
  • m-CBPQTの理想的なサイズと電子特性により,MS内の強い結合が可能である.
  • 発見は,新しい超分子組成の設計に洞察を与えます 根本的な相互作用に基づいています.