where does the Na bind to form the salt? On the NH2 or the SO2NH2?
(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)
Why is this?
Secondly, would it be correct to assume that the Sulfur containing substitute has something to do with the toxicity?
1) The reason why is explained in the PDF - it has to do with certain resonance structures.
2) I don't understand the question.
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..
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.
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?
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.
