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Topic: pKa hydroxybenzoates  (Read 4443 times)

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jeeftree

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pKa hydroxybenzoates
« on: July 12, 2006, 03:01:36 AM »
I can't find the pka of the OH group of hydroxybenzoates anywhere. Could someone please help me out. Thank you.

P.S.
I have checked the link in this forum. I have also checked the bordwell and evans pKa tables. They only give the pKa's for the COOH group.
« Last Edit: July 12, 2006, 06:38:52 AM by jeeftree »
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Offline Mitch

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Re: pKa hydroxybenzoates
« Reply #1 on: July 12, 2006, 05:04:59 AM »
Have you checked the pKa values link in our menu, its on the left side of your screen.
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Offline wereworm73

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Re: pKa hydroxybenzoates
« Reply #2 on: July 14, 2006, 04:20:16 PM »
Ok, here are the pKa2 values for the hydroxybenzoic acids:

o-hydroxybenzoic acid (salicylic acid):  13.4
m-hydroxybenzoic acid:  9.92
p-hydroxybenzoic acid:  9.32

The hydroxyl group on salicylic acid can form hydrogen bonds with the carboxylate group on the same molecule.  Because of this, the hydrogen doesn't leave so easily and its pKa is much higher.





 
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