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Topic: ESR naphthalene  (Read 4197 times)

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Offline AhmedEzatAlzawalaty

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ESR naphthalene
« on: March 26, 2007, 11:20:08 AM »
why ESR in naphthalene occurs at C1 and not C2 and when does it occurs at C2?
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Offline AhmedEzatAlzawalaty

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Re: ESR naphthalene
« Reply #1 on: March 27, 2007, 03:36:44 PM »
no i mean Electrophilic substitution reaction and not elimination substitution reaction
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Offline Sam (NG)

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Re: ESR naphthalene
« Reply #2 on: March 27, 2007, 07:42:48 PM »
Try drawing out resonance structures that stabilise the intermediate in each case, this should explain the trend (there are more for the C1 position).  This is also to do with the number of resonance structures that preserve aromaticity in the molecule.
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Offline madscientist

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Re: ESR naphthalene
« Reply #3 on: March 28, 2007, 12:38:36 AM »
Should have known that you meant Electrophilic substitution reaction  ::)

The vacant orbital on the electrophile finds it easier to overlap with the p-orbitals at the peri positions (C1, C4, C5, C8).  This is due to the fact that these orbitals contribute the most to the HOMO (psi 5).

The pic below is of the HOMO in naphthalene, notice the greater contribution at C1,C4,C5 & C8.

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