Substituent effects in free-radical reactions. A study of 4-substituted 3-cyanobenzyl free radicals was written by Fisher, T. H.;Meierhoefer, A. W.. And the article was included in Journal of Organic Chemistry in 1978.SDS of cas: 64113-86-6 This article mentions the following:
An extended Hammett treatment of the kinetics of N-bromosuccinimide bromination of I (R = H, halo, Me, Ph, MeO, NO2, PhN:N, CN, MeCO) led to a free radical substituent constant (锜介垾?. The substituent order of free-radical stabilization was F < MeO < Me < H < Cl < Ph < I < Br < NO2 < PhN:N < CN < MeCO. F and MeO destabilized the radical. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6SDS of cas: 64113-86-6).
5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 64113-86-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts