How does resonance affect basicity?

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How does resonance affect basicity?

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Answer 1 · 2015-10-31T15:36:08

In general resonance should decrease basicity. Why?

Explanation:

Resonance delocalizes electron density. As chemists, however, we should seek quantitative data. The $p K_{b}$ $pK_b$ of ammonia, $N H_{3}$ $NH_3$ , is 4.7. The $p K_{b}$ $pK_b$ of aniline (phenylamine), $C_{6} H_{5} N H_{2}$ $C_6H_5NH_2$ , is 9.42. Is this consistent with the statement above?

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How does resonance affect basicity?

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