The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Thermal reactions of organic nitrogen compound. I. I-Methylpyrrole》. Authors are Jacobson, I. A. Jr.; Heady, H. H.; Dinneen, G. U..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Application In Synthesis of 3-Methyl-1H-pyrrole. Through the article, more information about this compound (cas:616-43-3) is conveyed.
A flow method was used at 475-700°. At 475-575° the reaction was a homogeneous 1st-order isomerization, 1-methylpyrrole → 2-methylpyrrole → 3-methylpyrrole. The Arrhenius equation for this reaction, based on the disappearance of 1-methylpyrrole, is k = 2.39 × 1012e(-54,800/RT). Above 575° there was decomposition to give a complex mixture of reaction products.
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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