January 01, 2025, 03:28:19 PM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: pka of sulfolane  (Read 5526 times)

0 Members and 1 Guest are viewing this topic.

Offline adam

  • Regular Member
  • ***
  • Posts: 28
  • Mole Snacks: +1/-1
pka of sulfolane
« on: February 22, 2008, 12:34:41 PM »
Hi, I tried to find the pka of sulfolane (2,3,4,5-tetrahydrothiophene-1,1-dioxide), and I found in a canadian journal it's around 13. The pka of  diethyl sulfone is around 30-31.

¿¿¿Why the sulfolane is so acidic???
Which kind of stabilitzation of the resulting anion explain this dramatic change in acidity??
Thanks.

Logged

Offline movies

  • Organic Minion
  • Retired Staff
  • Sr. Member
  • *
  • Posts: 1973
  • Mole Snacks: +222/-21
  • Gender: Male
  • Better living through chemistry!
Re: pka of sulfolane
« Reply #1 on: February 22, 2008, 01:01:08 PM »
Are you sure that the two pKa values you found were measured in the same solvent?  Solvent has a huge effect!

My guess is the ~13 one was measured in water, but the ~30 one was measured in DMSO.
Logged

Offline adam

  • Regular Member
  • ***
  • Posts: 28
  • Mole Snacks: +1/-1
Re: pka of sulfolane
« Reply #2 on: February 22, 2008, 01:09:05 PM »
The canadian journal just give the value, the pka of diethylsulfone is in DMSO.
Where could I find the value of sulfolane in DMSO???

Thanks!
Logged

Offline movies

  • Organic Minion
  • Retired Staff
  • Sr. Member
  • *
  • Posts: 1973
  • Mole Snacks: +222/-21
  • Gender: Male
  • Better living through chemistry!
Re: pka of sulfolane
« Reply #3 on: February 22, 2008, 04:46:49 PM »
Hmm...none of my tables have the sulfolane on them.  I would check that paper you found again.  It may say somewhere in the experimental section how they determined the pKa, or maybe it will give a reference.
Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links