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Topic: Nitrogen groups attached to alkyl chain.  (Read 2733 times)

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Offline disillusioned19

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Nitrogen groups attached to alkyl chain.
« on: April 03, 2012, 09:26:25 AM »
Why is it when, say, an amine group is attached to a benzene ring, the nitrogen group is said to be electron donating, whereas when it is attached to an aliphatic chain it is considered electron withdrawing, like we see with negative inductive effect?

The same could be said of oxygen containing groups as well.

Thanks in advance.

Offline AWK

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Offline disillusioned19

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Re: Nitrogen groups attached to alkyl chain.
« Reply #2 on: April 03, 2012, 09:52:20 AM »
http://en.wikipedia.org/wiki/Inductive_effect
http://en.wikipedia.org/wiki/Mesomeric


I guess what you mean by this is that there is no resonance effect in an alkyl chain and so nitrogen cannot donate, only withdraw owing to its higher electronegativity than carbon?

Offline AWK

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Re: Nitrogen groups attached to alkyl chain.
« Reply #3 on: April 03, 2012, 11:02:42 AM »
In mesomeric effect it can donate.
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