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Topic: Aromatic vs. Anti-aromatic  (Read 13597 times)

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Offline fledarmus

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Re: Aromatic vs. Anti-aromatic
« Reply #15 on: August 05, 2011, 01:03:25 PM »
Looking at the original structure, I believe the resonance structure should have a negative charge on the carbon one step clockwise from where it is located in Opsomath's structure.

Offline opsomath

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Re: Aromatic vs. Anti-aromatic
« Reply #16 on: August 05, 2011, 01:16:52 PM »
There are quite a few valid resonance structures for this guy. I believe that if you can draw one that is aromatic, and one that is not, it will favor the one that is...just like cyclobutadiene can be antiaromatic or not aromatic, and distorts to favor the latter case.

Offline Honclbrif

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Re: Aromatic vs. Anti-aromatic
« Reply #17 on: August 05, 2011, 03:21:19 PM »
You can't just say it will favor the one that is aromatic if it is introducing other unfavorable interactions. By that logic, (1E,3Z,5E,7Z,9Z)-cyclodeca-1,3,5,7,9-pentaene should be aromatic too.

Your are arguing that this would exhibit fulvene-like aromaticity. My counter is that fulvene is only slightly aromatic* and that the introduction of an unfavorable interaction would make it less likely to be aromatic.

*UV-vis evidence that it is, but he ring current is almost unmeasurable by NMR
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Offline opsomath

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Re: Aromatic vs. Anti-aromatic
« Reply #18 on: August 05, 2011, 03:36:43 PM »
Honestly, I was assuming that the OP was correct, and looking for a reason to call it aromatic. If it ever was generated, probably by flash photolysis of something, it would probably be nonaromatic in terms of NMR. Similarly, a quantum chemical treatment with NICS would probably show no aromaticity.

Offline Honclbrif

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Re: Aromatic vs. Anti-aromatic
« Reply #19 on: August 05, 2011, 03:54:36 PM »
I'm going to have to ask the OP what their evidence for aromaticity is. Everything I can work out convinces me that it is either nonaromatic or antiaromatic.
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Offline orgopete

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Re: Aromatic vs. Anti-aromatic
« Reply #20 on: August 05, 2011, 07:37:43 PM »
I'm going to have to ask the OP what their evidence for aromaticity is. Everything I can work out convinces me that it is either nonaromatic or antiaromatic.

I'm with you. I used to make simple mistakes by doing a copy and paste. I can imagine some simple change was introduced without changing the aromaticity label. If this is supposed to be aromatic, I think this is a poor example to explain to rationalize it. Many students are confused by simple things like pyrrole or imidazole, why this example?

Fulvene ring current being virtually non-existant is a really good argument.
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