Sciencemadness Discussion Board

ammonium organic salts to amines to amine salts

underground - 25-8-2023 at 08:52

Ammonium organic salt form the coresponding amines upon heating, for example

ammonium formate --> formamide
ammonium acetate --> acetamide
ammonium oxalate --> oxamide e.t.c.

Have the nitrate/perchlorate salts of those amides ever studied ? Like formamide/acetamide nitrate/perchlorate oxamide dinitrate/diperchlorate ?

[Edited on 25-8-2023 by underground]

Microtek - 26-8-2023 at 02:33

Amides aren't very strong bases, so they don't form stable salts.

Texium - 26-8-2023 at 05:10

You’re gonna want to read up on some introductory organic chemistry. Amides have completely different reactivity than amines. I would suggest specifically reading up on the definitions of functional groups, and pKa.

[Edited on 8-26-2023 by Texium]

underground - 27-8-2023 at 06:44

I am pretty sure the perchlorate salts exist since perchloric acid is s strong acid. There was a topic in the past about oxamide dinitrate but it was not any deep investigation.

Texium - 27-8-2023 at 12:16

Maybe it can, but amides get protonated on the carbonyl oxygen, like other carbonyl compounds, not on nitrogen like amines.

Edit: and even if amides can be protonated by perchloric acid, it’s not gonna happen in an aqueous solution to a significant extent.

[Edited on 8-27-2023 by Texium]

DraconicAcid - 27-8-2023 at 12:20

I know you can make the salts of some amides- one of my labmates made acetamide hydrochloride once in grad studies. It turned out to be extremely hygroscopic and entirely unsuitable for whatever it was he wanted it for.

From here:

[Edited on 27-8-2023 by DraconicAcid]

AcetamideNitrate.JPG - 28kB