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Basic aqueous hybridization solution

Why are aniline (pWb = 9.4) and pyridine (pWb = 8.8) so much less basic than ammonia (pWb = 4.8) in aqueous solution For a long time, students of organic chemistry have been given reasons in terms of lone-pair delocalization and sp /sp hybridization of the nitrogen atom. From gas-phase studies, it is now clear that aniline and... [Pg.105]

In pyrrole (Fig. 14.21) the electrons are arranged differently. Because only four tt electrons are contributed by the carbon atoms of the pyrrole ring, the 5p -hybridized nitrogen must contribute two electrons to give an aromatic sextet. Because these electrons are a part of the aromatic sextet, they are not available for donation to a proton. Thus, in aqueous solution, pyrrole is not appreciably basic. [Pg.656]

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