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15 votes
1 answer
12k views

Why does hydrogen bonding in salicylic acid make it more acidic?

When salicylic acid deprotonates (losing the proton from the carboxyl group) it forms a hydrogen bond with between the oxygen in the carboxylate anion and the hydrogen in the alcohol group. However, ...
RobChem's user avatar
  • 9,802
5 votes
3 answers
5k views

Hydrogen bonding relating to molecular orbital theory

In [1, p. 232] here is an explanation of how alcohols hydrogen bond to each other and I do understand how the alcohols form hydrogen bonds to each other: FIGURE 6.15 Water and alcohols are both ...
Mousedorff's user avatar
12 votes
2 answers
2k views

Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?

If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows: Even after deprotonation, it has intramolecular hydrogen bonding as follows: My question: p-...
Neha's user avatar
  • 452
1 vote
1 answer
157 views

Why don't dicarboxylic acids show hydrogen bonding in spite of the fact that carboxylic acids exist usually as dimers in polar aprotic solvent? [closed]

I have seen several examples: The fact that maleic acid is more soluble in water than fumaric acid in spite of the fact that it must be able to show intramolecular hydrogen bonding. trans-...
Very Useless's user avatar