Is sulphonamide group prone to undergo diazotization?

Asked Jun 08 '21 at 13:23

Active Jun 09 '21 at 18:56

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I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one sulphonamide group is containing. Is the first reaction below correct?

Should it be essential not to have such group to have this reaction nicely going? - I mean getting only aromatic amine undergo diazotization.

edited Jun 09 '21 at 18:56

asked Jun 08 '21 at 13:23

Bencyklan

Sulphonamide is very different then amine - won't get protonated, much less nitrosated. – Mithoron Jun 08 '21 at 13:34
The -NH2 of the sulfonamide group is more acidic than basic so it is not going to protonate in the way you have drawn. – Waylander Jun 08 '21 at 13:36
So it won't protonate even if there is great excess of acid? I guess it will in THIS case. I mean in excess – Bencyklan Jun 08 '21 at 13:44
Think about how electron-withdrawing the sulfonyl group is. – Waylander Jun 08 '21 at 14:07
Ok, there is no problem because -NH2 from sulfonamid won't get easily protonated, so it won't react with HNO2 – Bencyklan Jun 08 '21 at 14:13

Is sulphonamide group prone to undergo diazotization?

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