Author Topic: Na binding to sulfanilamide  (Read 1363 times)

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jsorex

  • Guest
Na binding to sulfanilamide
« on: September 12, 2003, 11:23:00 AM »
where does the Na bind to form the salt? On the NH2 or the SO2NH2?


Rhodium

  • Guest
Sulfanilamide ion structure
« Reply #1 on: September 12, 2003, 07:16:00 PM »


Sulfanilamide is most easily deprotonated on the sulfonamide nitrogen:

http://acpcommunity.acp.edu/Facultystaff/hass/oc2web/Lab/exp/sulfa/exp4bg.pdf


jsorex

  • Guest
Why is this? Secondly, would it be correct to...
« Reply #2 on: September 13, 2003, 05:10:00 PM »
Why is this?
Secondly, would it be correct to assume that the Sulfur containing substitute has something to do with the toxicity?


Rhodium

  • Guest
sulfanilamide
« Reply #3 on: September 13, 2003, 05:18:00 PM »
1) The reason why is explained in the PDF - it has to do with certain resonance structures.

2) I don't understand the question.

jsorex

  • Guest
OK, thanks I'm reading the pdf right now.
« Reply #4 on: September 13, 2003, 05:22:00 PM »
OK, thanks I'm reading the pdf right now.

About the second question. Why is this substance toxic? I read somewhere (don't have refrence) that 100 people died in the 30's in the states cause of this drug..


jsorex

  • Guest
Ok apparently the poor water solubility is the
« Reply #5 on: September 13, 2003, 05:25:00 PM »
Ok apparently the poor water solubility is the reason of the nephrotoxicity. And thus droping the pKa will lesson the toxicity. Substituting the sulfoamide nitrogen atom.


Rhodium

  • Guest
Is there a limit to laziness?
« Reply #6 on: September 13, 2003, 05:52:00 PM »
OK, thanks I'm reading the pdf right now.

Huh? Didn't you even bother to read the reference I retrieved for you before asking more questions? Is there a limit to laziness?

jsorex

  • Guest
Re: Huh? Didn't you even bother to read the...
« Reply #7 on: September 15, 2003, 01:37:00 PM »

Huh? Didn't you even bother to read the reference I retrieved for you before asking more questions? Is there a limit to laziness?




Uh, in my case, no. Sorry, actually there's no point in asking anything, for all the answers one could find in either books, TFSE, via google etc.