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Features of Hydrogen Bonding

Hydrogen Bonding and acid strength

2-hydroxybenzoic acid
pKa= 2.98
3-hydroxybenzoic acid
pKa= 4.08
4-hydroxybenzoic acid
pKa= 4.58

Only the anion from the ortho-isomer is stabilized through hydrogen bonding thus responsible for greater acidity of the acid. This stabilization is not present in the other isomers due to unfavourable geometry.

Hydrogen Bonding and Acid Strength
hydrogen Bonding and Acid Strength
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