Related Experiment Video
Updated: Jun 10, 2026
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photochemistry and reactivity of the phenyl radical-water system: a matrix isolation and computational study
Artur Mardyukov1, Rachel Crespo-Otero, Elsa Sanchez-Garcia
1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, 44780 Bochum, Germany.
Abstract:
The reaction of the phenyl radical 1 with water has been investigated by using matrix isolation spectroscopy and quantum chemical calculations. The primary thermal product of the reaction between 1 and water is a weakly bound complex stabilized by an OH...pi interaction. This complex is photolabile, and visible-light irradiation (lambda>420 nm) results in hydrogen atom transfer from water to radical 1 and the formation of a highly labile complex between benzene and the OH radical. This complex is stable under the conditions of matrix isolation, however, continuous irradiation with lambda>420 nm light results in the complete destruction of the aromatic system and formation of an acylic unsaturated ketene. The mechanisms of all reaction steps are discussed in the light of ab initio and DFT calculations.
Related Concept Videos
Radical Reactivity: Steric Effects
Along with electronic factors, steric factors also account...
Radical Reactivity: Overview
Radical Reactivity: Electrophilic Radicals
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Radical Reactivity: Intramolecular vs Intermolecular
Radical Reactivity: Nucleophilic Radicals

