In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Deprotonation of Methyl-Substituted, Five-Membered Aromatic Molecules: A Surprising Case of Mixed Conjugation, Rehybridization, and Induction Contributions, published in 2014-09-05, which mentions a compound: 616-43-3, mainly applied to methyl substituent aromatic deprotonation conjugation rehybridization induction DFT MP2, Name: 3-Methyl-1H-pyrrole.
Methyl-substituted, six-membered aromatic mols. are deprotonated to benzylic carbanions, which are stabilized by π conjugation. In contrast, deprotonation of 3(5)-methylpyrazole (NH protected) occurs at an endocylic CH group. Computational analyses showed that the reduction of π conjugation in substituted five-membered rings plays a major role, while the reduced bond angles, in addition to the strengthened induction of Csp2 vs. Csp3, further favor the deprotonation of endocyclic carbon sites rather than that of the Me group.
This literature about this compound(616-43-3)Name: 3-Methyl-1H-pyrrolehas given us a lot of inspiration, and I hope that the research on this compound(3-Methyl-1H-pyrrole) can be further advanced. Maybe we can get more compounds in a similar way.
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