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Topic: Ring activators  (Read 2534 times)

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Offline neobenzene

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Ring activators
« on: October 23, 2012, 10:38:30 AM »
Why is the phenoxide ion a better ring activator than phenol? Is it because of the negative charge on the phenoxide ion?
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Offline discodermolide

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Re: Ring activators
« Reply #1 on: October 23, 2012, 10:42:21 AM »
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Offline neobenzene

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Re: Ring activators
« Reply #2 on: October 23, 2012, 10:50:49 AM »
Thank you! That was a very useful link. But I didn't understand one thing. I'll quote from that link

"The negative charge in phenoxide ion is stabilized by solvation and by electron delocalisation into the ring"
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Offline discodermolide

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Re: Ring activators
« Reply #3 on: October 23, 2012, 10:56:15 AM »
So what's not to understand? Draw some resonance structures delocalising the negative charge into the ring.
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Offline neobenzene

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Re: Ring activators
« Reply #4 on: October 23, 2012, 10:59:04 AM »
OK...I did the resonance. But I didn't understand what it has to do with solvation.
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Offline discodermolide

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Re: Ring activators
« Reply #5 on: October 23, 2012, 11:01:58 AM »
The solvent molecules e.g.water hydrogen bond to the negative charge and help stabilise it.
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Offline neobenzene

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Re: Ring activators
« Reply #6 on: October 23, 2012, 11:03:20 AM »
Ok...got it  :D Thank you!
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