The Vespiary

The Hive => Newbee Forum => Topic started by: jsorex on September 12, 2003, 11:23:00 AM

Title: Na binding to sulfanilamide
Post by: jsorex on September 12, 2003, 11:23:00 AM
where does the Na bind to form the salt? On the NH2 or the SO2NH2?

Title: Sulfanilamide ion structure
Post by: Rhodium on September 12, 2003, 07:16:00 PM
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458597-file_nsms.gif)

Sulfanilamide is most easily deprotonated on the sulfonamide nitrogen:

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

Title: Why is this? Secondly, would it be correct to...
Post by: jsorex 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?

Title: sulfanilamide
Post by: Rhodium 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.
Title: OK, thanks I'm reading the pdf right now.
Post by: jsorex 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..

Title: Ok apparently the poor water solubility is the
Post by: jsorex 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.

Title: Is there a limit to laziness?
Post by: Rhodium 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?
Title: Re: Huh? Didn't you even bother to read the...
Post by: jsorex 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.