The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Polarographic reducibility of pyrrole and pyrrole substitutes》. Authors are Bonino, G. B..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Name: 3-Methyl-1H-pyrrole. Through the article, more information about this compound (cas:616-43-3) is conveyed.
cf. C.A. 38, 1230.6. 1-Methylpyrrole, 2-methylpyrrole, 1-allylpyrrole, 2,4-dimethylpyrrole, 2,5-dimethylpyrrole, 3-methylpyrrole, 4-ethylpyrrole, 2,3,5-trimethylpyrrole, 2,5-dimethylpyrrole, 3-ethylpyrrole, 2,4-dimethylpyrrole, and pure 2,3,4,5-tetramethylpyrrole (I) (the latter obtained by the action of K methylate on trimethylpyrrole) in 0.1 N LiCl solution in 80% EtOH were not reduced polarographically. I obtained by the Piloty and Hirsch method (cf. C.A. 7, 1365), containing tetramethylpyrazine (II) as an impurity, showed the same polarographic wave of reduction as II. The findings of Dezelic (Boll. intern. acad. croata sci. e belle arti, 1941) are not correct.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate