Related Experiment Video
Updated: Feb 2, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Stable (BIII -Subporphyrin-5-yl)dicyanomethyl Radicals
Bellamkonda Adinarayana1, Daiki Shimizu1, Atsuhiro Osuka1
1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
Abstract:
Stable BIII -subporphyrin-substituted dicyanomethyl radicals were synthesized by SN Ar reaction of meso-bromo- or meso-chlorosubporphyrins with malononitrile followed by oxidation with PbO2 . Different from previously reported dicyanomethyl radicals that underwent σ- or π-dimer formation both in the solid state and in solutions, subporphyrin-stabilized dicyanomethyl radicals exist as monomers in solutions even at low temperature. DFT calculations revealed efficient spin delocalization over the entire subporphyrin. In the solid state, these radicals form weak π-dimers with antiferromagnetic interactions depending on the crystal packing structures.
Related Concept Videos
5-Number Summary
In a box plot, the minimum and maximum data values represent the lower and upper whiskers in the graph, and the median is designated as the center of the box in the chart. The first quartile and third...
Radical Reactivity: Electrophilic Radicals
Radical Reactivity: Nucleophilic Radicals
Radicals
Radical Equations
Radical Autoxidation

