An NMR investigation of ground-state polarization of some substituted aromatic systems was written by Collins, Michael J.;Hatton, Paul M.;Sternhell, Sever. And the article was included in Australian Journal of Chemistry in 1992.Recommanded Product: 5-Methyl-2-nitrobenzonitrile This article mentions the following:
A previously established NMR method for estimating mobile bond orders was used to examine the ground-state polarization of benzene or heteroaromatic derivatives with ortho or para pairs of +R/-R substituents in benzene, naphthalene, furan, thiophene, pyrrole, quinoline, and pyrazole systems. Evidence for significant ground-state polarization which is solvent-independent was observed in these systems, especially benzene, pyrrole, and pyrazole. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 5-Methyl-2-nitrobenzonitrile).
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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 5-Methyl-2-nitrobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts