Acids question Watch

alevels2k17
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#1
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Why is para - amino benzoic acid considered acidic??? It has both a cooh group and an amino group! Isn't it supposed to be a zwitterion?
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Pigster
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Do you know about the basicity of aminobenzene compared to non-aromatic amines?

Do you know about the basicity of amines compared to the acidity of carboxylic acids?
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ChemistryWebsite
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A molecule being acidic and a molecule existing as a zwitterion are not mutually exclusive. After all, amino acid zwitterions behave as acids. (Just because the proton isn't being lost from the -COOH doesn't mean its not acidic).

A quick look on google suggests amino benzoic acid does form a zwitterion.
The lone pair on the amine group's nitrogen is partially delocalised into the aromatic system, suggesting that the proton of the zwitterion form will be quite easily lost relative to protonated aliphatic amines.
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