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Topic: ranking basicity in heteroatoms  (Read 4906 times)

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Offline black_squirrel

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ranking basicity in heteroatoms
« on: November 29, 2007, 01:00:36 AM »
This was on my recent test. I got the middle two right but I had the leftmost and right most switched. high number means more basic. why is the left one more basic than the right one?
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Offline ultrashogun

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Re: ranking basicity in heteroatoms
« Reply #1 on: November 29, 2007, 12:29:41 PM »
In the left structure the top nitrogen is sp2 and it can delocalize  its lone pair into the ring. Its less basic for the same reason that fenol is more acidic than an alcohol.
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Offline black_squirrel

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Re: ranking basicity in heteroatoms
« Reply #2 on: November 29, 2007, 06:32:50 PM »
OHH wow. the -NH2 is obviously more acidic than the nitrogen in the ring. i totally overlooked the fact that it was a nitrogen and was comparing nitrogens in the ring only.
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