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Topic: Is the Nitrogen in a Pyrimidine ring electron donating or withdrawing?  (Read 2061 times)

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Offline Zensation

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Is the Nitrogen in a Pyrimidine ring electron donating or withdrawing?
« on: June 02, 2014, 04:15:22 PM »
Sort of confused here. I am inclined to think it is electron withdrawing since the pKa is so low, but I've never really understood how Nitrogen or NH on a ring can be electron withdrawing. Aren't amines typically nucleophilic? Does the absense of 1 or more hydrogen increase the electrophilicity? 
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Offline Hunter2

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Re: Is the Nitrogen in a Pyrimidine ring electron donating or withdrawing?
« Reply #1 on: June 03, 2014, 09:02:04 AM »
It is donating. It is not part of the aromatic system. Difference to Pyrrol, where it is part fhe aromatic system.
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