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関連する概念動画

Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
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...
2.1K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.9K
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...
4.9K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
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...
2.6K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.4K
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...
2.4K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.7K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.7K
π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

4.4K
Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.4K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

12.1K

Conformation-Variable [7]Annulenyl Radicals

Guantao Yang1, Lingfang Chen2,3, Zhizhe Liu1

  • 1Beijing National Laboratory For Molecular Sciences, Centre For the Soft Matter Science and Engineering, College of Chemistry, the Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, Peking University, Beijing, P. R. China.

Chemistry (Weinheim an der Bergstrasse, Germany)
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PubMed
まとめ
この要約は機械生成です。

研究者らは新規ベンゾ縮合[7]アニュレニルラジカルを合成した。分子構造はラジカルの安定性とスピン分布に大きく影響し、平面構造と特定の置換基が永続性を高めることが示された。

キーワード:
七員環埋め込みラジカル有機ラジカル安定性

さらに関連する動画

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization
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Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization

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関連する実験動画

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization
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科学分野:

  • 有機化学
  • 材料科学
  • 物理化学

背景:

  • ベンゾ縮合[7]アニュレニルラジカルは、そのユニークな電子的および構造的特性により関心を集めている。
  • 分子構造とラジカル安定性の関係を理解することは、新しい材料を設計する上で重要である。

研究 の 目的:

  • 一連のベンゾ縮合[7]アニュレニルラジカル誘導体を合成し、調査すること。
  • 分子構造の変化がスピン分布とラジカルの永続性にどのように影響するかを明らかにすること。

主な方法:

  • 新規ベンゾ縮合[7]アニュレニルラジカル誘導体の合成。
  • スピン分布の解析のための電子常磁性共鳴（EPR）分光法。
  • 実験結果を支持するための計算化学的手法。

主要な成果:

  • 無置換ラジカルでは、スピンが非局在化した平面ジベンゾ[a,d][7]アニュレニル骨格が同定された。
  • ラジカルの永続性は置換基によって異なり、トリイソプロピルフェニル置換ラジカルは半減期が23時間であった。
  • C10位の置換基は安定性を向上させたが、わずかな湾曲を引き起こした。一方、トリベンゾ[a,c,e][7]アニュレニルラジカルは、非平面構造のため安定性が低かった。
  • C9位へのアンスリル基の導入は、コンフォメーション変化とスピンのアンソリレンユニットへの再配置を引き起こした。

結論:

  • 分子構造、特に平面性と立体障害は、ベンゾ縮合[7]アニュレニルラジカルの安定性とスピン特性に決定的に影響する。
  • 戦略的な置換はラジカルの永続性を高めることができるが、非平面構造は安定性を著しく低下させ、スピン局在化を変化させる可能性がある。
  • コンフォメーションの柔軟性と置換基効果は、これらのラジカル系の特性を調整するための経路を提供する。
  • 有機化学
  • 材料科学
  • 物理化学