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Topic: Basicity of amine groups  (Read 2315 times)

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Offline bmilla35

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Basicity of amine groups
« on: December 08, 2011, 11:02:53 PM »
Well, I doubt i'm right, but I tried! We've done a similar example but I still don't quite understand it. (Actually, I don't even know if I did the resonance structures right.) I do see how the positive and negative charge stabilize each other, but there's also a second positive charge right next to it...ahh!!

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Offline Dan

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Re: Basicity of amine groups
« Reply #1 on: December 09, 2011, 03:54:59 AM »
Your resonance structures are fine, and the argument is logical.
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Offline bmilla35

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Re: Basicity of amine groups
« Reply #2 on: December 09, 2011, 07:52:12 AM »
Quote from: Dan on December 09, 2011, 03:54:59 AM
Your resonance structures are fine, and the argument is logical.

Thank you!
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Offline spirochete

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Re: Basicity of amine groups
« Reply #3 on: December 16, 2011, 09:03:06 PM »
Your answer is good, but for completeness I would also note that Methyl is electron donating as well, by hyperconjugation.  It's just that the ortho-amine substitutent is even more electron donating, thus making the indicated molecule a stronger base.
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