Rich_Insane - 20-12-2012 at 20:33
Hey everyone,
I have a quick question: Will sodium bicarbonate work as an agent to deprotonate hydroxylammonium chloride? I have a reference which uses sodium
acetate to deprotonate hydroxylammonium chloride (and prevent it from forming again), but I am out of anhydrous sodium acetate and only have baking
soda around. I know that sodium acetate is a weaker base than NaHCO3, so my guess is that it will be an appropriate substitute. Any ideas?
unionised - 21-12-2012 at 05:01
Got any vinegar?
Rich_Insane - 21-12-2012 at 09:53
I have vinegar and I have a limited amount of acetic anhydride, but I hear that getting anhydrous sodium acetate from vinegar/bicarb is not
an easy task...
BlackDragon2712 - 22-12-2012 at 18:19
sodium butan-1-olate can be use to deprotonate the Hydroxylammonium chloride but it's not easy to get, perhaps backing soda will work just fine but
I'm not sure. the best would be get some acetic acid and make the synthesis of the sodium acetate, but then it would be way better buy it directly xD
making sodium acetate from vinager is dificult because of the impurities of the vinegar, if you get a vinager pure enough then it may work very easy.
but well, i'm just giving ideas 
xd
[Edited on 22/12/2012 by BlackDragon2712]
[Edited on 22/12/2012 by BlackDragon2712]
thoriumthorium - 28-12-2012 at 14:26
What are you trying to do? Baking soda will just give you the free base. It's not strong enough at all to deprotonate hydroxylamine. In fact the
opposite will occur.
Rich_Insane - 28-12-2012 at 15:57
Deprotonate NH2OH.HCl to the freebase. Standard procedure for preparing oximes utilizes NaOH (I've also seen NaOAc) as a base to deprotonate NH2OH.HCl
to the free amine (which is the nucleophile in the reaction). However, say your carbonyl compounds is sensitive to NaOH. Will NaHCO3 act as a
substitute to both pull off the proton on the quaternary amine (HONH3+) and prevent the oxime from deoximating ?