Are either of the nitrogens conjugated with the benzene ring? briefly explain i

Question

Are either of the nitrogens conjugated with the benzene ring? briefly explain

i know the double bonds are alternating and the two nitrogens are in resonance with one another, so it should be in conjugation... but do the electrons in benzene not leave since it would mess up the aromaticity?

Are either of the nitrogens conjugated with the benzene ring? briefly explain i know the double bonds are alternating and the two nitrogens are in resonance with one another, so it should be in conjugation... but do the electrons in benzene not leave since it would mess up the aromaticity?

Explanation / Answer

No, none of the two nitrogens is conjugated with the benzene ring.

If we try to write a resonating structure with the Nitrogens in conjugation with the Benzene ring the resulting structures will be highly unstable as we'll have +ve charge over Nitrogen and sp hybridisation in a ring struture which causes a lot of angular distortion. It also leads lo loss of aromaticity.

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