Sign In

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 for the stability of these persistent radicals. For instance, the exceptionally high stability of triphenylmethyl radical is due to the presence of three surrounding phenyl rings that are twisted out of the plane by 30° in a propeller conformation. These twisted phenyl rings sterically shield the central carbon, which bears most of the radical character. As a result, the radical becomes highly stable and unavailable for molecules to react. Therefore, steric hindrance imparts stability to the radicals making them less reactive.

Tags
Radical ReactivitySteric EffectsElectron donating GroupsElectron withdrawing GroupsConjugating GroupsElectronically stabilized RadicalsPersistent RadicalsTriphenylmethyl RadicalTetramethylpiperidine N oxide22 diphenyl 1 picrylhydrazylSteric HindranceRadical StabilityPhenyl RingsPropeller Conformation

From Chapter undefined:

article

Now Playing

Radical Reactivity: Steric Effects

Related Videos

1.7K Views

article

Radicals: Electronic Structure and Geometry

Related Videos

3.1K Views

article

Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals

Related Videos

2.1K Views

article

Radical Formation: Overview

Related Videos

1.8K Views

article

Radical Formation: Homolysis

Related Videos

2.7K Views

article

Radical Formation: Abstraction

Related Videos

2.8K Views

article

Radical Formation: Addition

Related Videos

1.5K Views

article

Radical Formation: Elimination

Related Videos

1.5K Views

article

Radical Reactivity: Overview

Related Videos

1.7K Views

article

Radical Reactivity: Concentration Effects

Related Videos

1.4K Views

article

Radical Reactivity: Electrophilic Radicals

Related Videos

1.7K Views

article

Radical Reactivity: Nucleophilic Radicals

Related Videos

1.8K Views

article

Radical Reactivity: Intramolecular vs Intermolecular

Related Videos

1.6K Views

article

Radical Autoxidation

Related Videos

1.7K Views

article

Radical Oxidation of Allylic and Benzylic Alcohols

Related Videos

1.6K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2024 MyJoVE Corporation. All rights reserved