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

2.78 : Given the structure above for the basic red dye 1. The resonace structure is drawn which is very conjugated system and thus the dye is very effective.

The ring that does not participate in the resonance effectively would be the one with the ester functionality attached to it. This ring will have less electron density as compared to the other rings with electron donating Nitrogen and oxygen both of which are donating electrons by resonance and enhance resonance effect in the dye molecule.

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