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Related Concept Videos

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
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 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: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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 instance, consider...
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...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Higher Excited-State Reactivity of a Charge-Neutral Organic Radical.

Elena Bassan1, Bruno Lazarevski1, Oliver S Wenger1

  • 1Department of Chemistry, University of Basel, 4056 Basel, Switzerland.

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Neutral organic radicals can be reactive in upper excited states, unlike typical photochemical behavior. This finding impacts photoredox catalysis and synthetic chemistry.

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Area of Science:

  • Photochemistry
  • Organic Chemistry
  • Catalysis

Background:

  • Photoredox catalysis often focuses on radical ions, leaving neutral organic radicals less explored.
  • Understanding excited state reactivity is crucial for advancing photoredox catalysis.

Purpose of the Study:

  • To investigate the photochemical reactivity of neutral boryl radicals.
  • To explore the influence of different light wavelengths on radical reactivity.
  • To elucidate the mechanistic pathways in borylation reactions.

Main Methods:

  • Direct laser spectroscopy to observe excited states.
  • Transient absorption spectroscopy to study radical reactivity.
  • Mechanistic studies on boryl radical regeneration.

Main Results:

  • Neutral boryl radicals are unreactive in their lowest excited state (red light).
  • Boryl radicals can initiate photoreduction from upper excited states (blue light).
  • In-cage charge recombination influences photoreaction quantum yields.

Conclusions:

  • Excited state reactivity of neutral radicals deviates from the norm.
  • Mechanistic insights enable catalytic turnover in borylation reactions.
  • Findings have broad implications for photochemistry and artificial photosynthesis.