Imidazole is an aromatic ring in the side chain of the amino acid histidine, which is present in nearly all proteins. It has two nitrogen atoms. ... However, imidazole is about 100 times more basic than pyridine. The increased basicity results from resonance stabilization of the charge to both nitrogen atoms.
Why is imidazole so basic?
Explain why N1 of imidazole is most basic
In the cyclic structure, there are 2 pi bonds (between C2-C3 and N1-C5) and one lone pair on N4 that can interact with each other to form a delocalised pi system. ... This means that like bezene, imidazole has a closed delocalised ring of 6 pi electrons.
Why is imidazole more basic than pyrrole?
Imidazole is over a million times more basic than pyrrole because the sp2 nitrogen that is part of one double bond is structurally similar to pyridine, and has a comparable basicity.
