Basic red 1 is a tetracyclic compound (it has four rings) that shares many struc

Question

Basic red 1 is a tetracyclic compound (it has four rings) that shares many structural similarities with the dyes in the previous problem (Chem. Rev. 1993, 93, 381-433). This compound has many significant resonance structures, and the positive charge is highly delocalized. While resonance structures can be drawn in which the positive charge is spread throughout all four rings, nonetheless, one of the rings likely bears very little of the charge relative to the other rings. Identify the ring that is not participating as effectively in resonance and suggest an explanation.

Explanation / Answer

Resonace is essentially the flow of electrons in Pi bonds...

Thereofre:

The ring that has the least resonance must be the one in the right (top)

Note that the most resonance structure ring are

The left ring ( completely filled of pi bonds, which allow it to be aromatic)

The bottom ring ( completely filled of pi bonds, which allow it to be aromatic)

There is also resonance in the center ring, even though it does NOT appears to have more than 1 pi bond, it DOES has, since the left ring provides one pi bnond, and th eoxygen has lone pairs

Therefore, the right ring is the least charged/resonance ring

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