Describe the basic strength of aryl amine compounds relative to a… - Vidyadip

Question

Describe the basic strength of aryl amine compounds relative to ammonia.

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Answer

→In aniline or other arylamines, the - NH₂ group is attached directly to the benzene ring. It results in the unshared electron pair on nitrogen atom to be in conjugation with the benzene ring and thus making it less available for protonation.
→Five resonance Hybrid structures of aniline are as following:

→On the other hand, anilinium cation obtained by accepting a proton can have only two resonat- ing structures.

→We know that greater the number of resonating structures greater is the stability, thus aniline is more stable than anilinium ion.
→Hence, the proton acceptability or the basic na- ture of aniline or other aromatic amines would be less than that ammonia.
→In case of substituted aniline, it is observed that electron releasing groups like $- OCH _3,- CH _3$ increase basic strength where as electron with-drawing groups like $- NO _2,- SO _3 H ,- COOH$, -X decrease it.

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