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Radical Reactivity: Overview

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: Homolysis

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 Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

Radical Reactivity: Electrophilic Radicals

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 Halogenation: Thermodynamics

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy between bonds broken and bonds...

Radical Formation: Abstraction

Radical Formation: Abstraction

The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...

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Related Experiment Video

Updated: Jun 8, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

HOCO radical chemistry.

Joseph S Francisco¹, James T Muckerman, Hua-Gen Yu

¹Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. francisc@purdue.edu

Accounts of Chemical Research

|October 9, 2010

Summary

This summary is machine-generated.

The HOCO radical, crucial in atmospheric and combustion chemistry, has two stable forms, trans- and cis-HOCO. Its reactivity and role in converting CO to CO2 are now better understood through theoretical and experimental studies.

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Last Updated: Jun 8, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Published on: April 19, 2019

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

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Published on: April 24, 2014

Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization

Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization

Published on: August 6, 2018

Area of Science:

Atmospheric Chemistry
Combustion Science
Chemical Physics

Background:

Free radicals are key species in atmospheric chemistry, combustion, plasma, interstellar clouds, and biochemistry.
Understanding radical formation, structure, stability, reactivity, spectroscopy, and dynamics is vital.
The HOCO radical is significant in atmospheric and combustion environments, particularly in CO to CO2 conversion.

Purpose of the Study:

To systematically review the current knowledge of the HOCO radical.
To detail recent theoretical and experimental findings on HOCO.
To elucidate the chemical role and properties of the HOCO radical.

Main Methods:

High-level ab initio calculations to identify stable conformers.
Experimental spectroscopy to confirm radical structures.
Analysis of reaction mechanisms and rates.

Main Results:

Identified two stable conformers: trans-HOCO (more stable) and cis-HOCO.
Determined the heat of formation for HOCO (298 K) as -43.0 ± 0.5 kcal/mol.
Characterized HOCO reactivity, noting hydrogen donation in reactions with atoms via association and elimination pathways.

Conclusions:

The HOCO radical's structure, stability, and reactivity are now better understood.
trans-HOCO is the more stable conformer.
HOCO exhibits significant reactivity, often acting as a hydrogen donor in chemical reactions.