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Author: Subject: Are all formamids unstable in the prescense of water?
Electra
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[*] posted on 12-4-2016 at 21:33
Are all formamids unstable in the prescense of water?


I've read that normal formamide is unstable in water and hydrolyzes (or am I mistaken?), but does this happen to substituted (alkyl and alkyl-aryl) formamides as well? Or do substituted formamides behave like any other amide around water?

[Edited on 13-4-2016 by Electra]
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Dr.Bob
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[*] posted on 13-4-2016 at 07:02


Formamides covers a lot of ground, but I have made some in the past, of alkyl amines, and they are stable to water for short times, like extractions and reaction workups. Most will slowly hydrolyze in water or humid air, but not quickly. I have actually had some hindered ones that take boiling 6N HCl to hydrolyze, which is pretty harsh. And DMF (dimethylformamide) is pretty water stable, although I rarely leave it mixed in water except when I am trying to wash it away from a reaction workup.
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Electra
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[*] posted on 13-4-2016 at 11:39


I am guessing the hydrolysis would occur by nucleophilic attack of the water, so maybe if the molecule is electron rich enough, it could be stabilized.
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