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Imidazole vs Pyrrolidine Basicity

bzk
in Inorganic Chemistry

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Hi everyone. I had a question concerning the basicity of nitrogens in Imidazole ( 2 nitrogens) vs the basicity in the 1 nitrogen in Pyrrolidine.

 

I understand that the nitrogen not attached to the hydrogen in Imidazole is the most basic of the 3 because of the lone pair that is in the same plane of the aromatic system. However, I was stuck on the LEAST basic nitrogen of the 3. I know the lone pair of second nitrogen in Imidazole is in the plane of the aromatic system, but not sure about the lone pair of the nitrogen in Pyrrolidine. Any help is greatly appreciated. Thanks!

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