Na binding to sulfanilamide

[jsorex]

where does the Na bind to form the salt? On the NH2 or the SO2NH2?

[Rhodium]

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458597-file_nsms.gif" title="View this image">

Sulfanilamide is most easily deprotonated on the sulfonamide nitrogen:

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

[jsorex]

Why is this?
Secondly, would it be correct to assume that the Sulfur containing substitute has something to do with the toxicity?

[Rhodium]

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]

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]

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]

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]

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.