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Stability of phenyl cation

  1. May 23, 2012 #1
    In my book, it's written that the phenyl cation can't be stabilized by resonance. I can't think of any reason why this is so. All the conditions for resonance are satisfied : all carbon atoms lie in one plane, all possible canonical structures will have the same number of unpaired electrons, we'll only move the pi - electrons.
    Also, I think that the carbon atom having positive charge must be sp - hybridized, as per the orbital diagram, but I guess even that is incorrect. Can anyone explain this???
  2. jcsd
  3. May 23, 2012 #2
    Try drawing out the resonance structures.
  4. May 24, 2012 #3
    The only way to rearrange a phenyl cation would be a hydride shift, which is unfavorable.
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