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Topic: pKa values of hydroxybenzoic acids  (Read 2536 times)

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Offline kahynickel

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pKa values of hydroxybenzoic acids
« on: June 19, 2015, 07:23:17 AM »
2-hydroxybenzoic acid is more acidic (pKa = 3.0) than 4-hydroxybenzoic acid (pKa = 4.6). Both can be deprotonated from COOH group to produce COO- but why the prior is more acidic

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« Last Edit: June 19, 2015, 09:27:01 AM by sjb »
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Offline mjc123

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pKa values of hydroxybenzoic acids
« Reply #1 on: June 19, 2015, 08:21:31 AM »
The COO- is stabilized by intramolecular hydrogen bonding with the ortho OH group.
« Last Edit: June 19, 2015, 09:26:33 AM by sjb »
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