[Peacock]

Hi!
How stable is such thing?

Would it be as simple as performing an oxime reaction with a carboxylic acid?
I don't see anything like this...which makes me think it is not stable 

Does anybody know anything about this?

Regards

[sjb]

Hi!
How stable is such thing?

Would it be as simple as performing an oxime reaction with a carboxylic acid?
I don't see anything like this...which makes me think it is not stable 

Does anybody know anything about this?

Regards

How do you intend forming it? Surely something like hydroxylamine on a naked acid will simply get protonated and thence unreactive?

[Peacock]

Could such thing be synthesized at an appropriate pH then?

[sjb]

Could such thing be synthesized at an appropriate pH then?

I don't think so, or at least every time I doodle around with this I end up with a hydroxamic acid (http://goldbook.iupac.org/H02911.html).

[orgopete]

Hydroxylamine with an ester will give a hydroxamic acid. The conditions for neutralizing hydroxylamine are mild.

[karlosshughes]

An oxime is a compound with a C=N(OH) group in it.

Like with any amine, reacting hydroxylamine with a carboxylic acid would just result in the ammoium carboxylate salt.

Reacting this with an acid derivative such as an acid chloride or anhydride would produce an amide.

Hence, an oxime can only be produced from an aldehyde or ketone.