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Quoting from my textbook:

Although stabilized by resonance compared with other carbocations, its resonance energy is much less than that of the starting benzene ring.

Here is more context :


textbook passage on the benzenonium ion, showing its canonical forms


Isn't that good? Isn't it more stable if it had less energy? Shouldn't it stay that way?

I feel like I'm missing something very obvious but I can't pinpoint it.

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    $\begingroup$ Maybe try suggesting an alternative next time :) $\endgroup$
    – Alara
    Apr 29, 2020 at 23:03
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    $\begingroup$ It is potentially badly worded. Resonance energy is a negative quantity: it is how much more stable something is compared to the alternative (benzene is more stable than the theoretical cyclohexatriene with three double and three single bonds). But benzenonium ions have less resonance energy than benzene but more than other carbocations so have higher energy than benzene but lower energy than typical carbocations. $\endgroup$
    – matt_black
    Apr 30, 2020 at 11:10
  • $\begingroup$ I would not even say that is poorly worded. $\endgroup$
    – Alchimista
    May 3, 2020 at 9:30

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