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Topic: Why is aminobenzene less basic than cyclohexylamine?  (Read 3230 times)

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Offline derek0o0

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Why is aminobenzene less basic than cyclohexylamine?
« on: February 12, 2009, 03:05:33 PM »
Why is aminobenzene less basic than cyclohexylamine?
It must be soemthing do with the benzene ring which the electrons are delocalised into it
But how can I explain this?

Offline macman104

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Re: Why is aminobenzene less basic than cyclohexylamine?
« Reply #1 on: February 12, 2009, 03:52:31 PM »
That is exactly why.  The lone pair, which the nitrogen uses to attract a proton is delocalized into the ring system.  It has less "lone-pair character" you might say, so it behaves less like a base.

Side note, I'm gonna move this over to organic chem

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