Why is imidazole (C3H4N2) aromatic?
1 Answer
Well, the requirements for aromaticity are:
- Planar ring
#4n + 2# #pi# electrons- Delocalization of electrons throughout the ring (i.e. conjugated
#pi# system)
Drawing out imidazole, we get:
LOCALIZED VS. DELOCALIZED
I would examine the electron geometries to check whether or not all the lone pairs of electrons supposedly conjugated throughout the system are in an orbital that is perpendicular to the ring, NOT parallel (if electrons are in a parallel orbital, they are localized outside of the otherwise aromatic ring).
We see two lone pairs. The upper right nitrogen has an
HÜCKEL'S RULE
So, imidazole has two
PLANARITY
Next, we know this is a planar ring because we have two
CONJUGATED
Finally, drawing the resonance structures, we get:
thus showing full conjugation throughout the