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Author: Subject: Copper nitrourea/nitroguanidine nitrates
Yorty2040
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[*] posted on 22-4-2024 at 11:50
Copper nitrourea/nitroguanidine nitrates


I've looked through all the previous threads on the boards and can't find anything about these compounds, or how to make them.

Seeing if a secondary could be made into a primary by complexing it with a metal salt would be interesting. I'm sure it's been done before, but I'm also wondering if the nitrourea complex would be less susceptible to hydrolysis and more stable in storage than the uncomplexed nitrourea.

It would be interesting to see if a good primary could be made out of either. Is it as simple as mixing a hot aqueous solution of copper nitrate with a hot aqueous solution of nitrourea or nitroguanidine (with a mass ratio of 0.9g Cu(NO3)2 per 1g NU/NQ) and allowing it to cool?

I found and attached a PDF with some solubility data regarding NU and UNi which indicates NU is actually more soluble in methanol than it is in water, but it seems to only have data for STP, not elevated T.

And of course I have no idea regarding the solubility of the complexes or how stable they are, either chemically or physically. I would like at least a little guidance so I'm not flying in completely blind.

Attachment: UNi and NU data (1MB)
This file has been downloaded 40 times

[Edited on 23-4-2024 by Yorty2040]

[Edited on 23-4-2024 by Yorty2040]
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[*] posted on 22-4-2024 at 14:09


In order to complex, it has to be basic in ph. Aminourea for example can be complexed cause it is basic but nitrourea is acidic. Also nitrourea is not that stable. Even if nitrourea could be complexed it would be quite unstable. Aminonitrourea could be possible to complex but quite complicated to produce.

There are plenty of other well known primaries out there that imho does not worth the trouble.
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Yorty2040
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[*] posted on 22-4-2024 at 18:42


Could nitroguanidine form a complex? I know it's basic enough to form salts with nitric and perchloric acid, though they're not very stable and sometimes decompose if you try to recrystallize and dry them incorrectly...

[Edited on 23-4-2024 by Yorty2040]
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[*] posted on 23-4-2024 at 04:23


Yea NQ can form complex

https://youtube.com/watch?v=Wrz6UL2C3Zw&pp=ygUWTml0cm9nd...
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Yorty2040
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[*] posted on 23-4-2024 at 08:18


So the aci-nitro tautomer of nitroguanidine is deprotonated in aqueous NaOH, and the solution of sodium nitroguanidinate is added to a solution of the metal salt to form the complex?

I know nitroguanidine is hydrolyzed in alkaline media, but if the temperature is low the decomposition is minimal in the timeframe shown in the video.

Why wouldn't this work for nitrourea? The nitramine should tautomerize just like NQ, and the aci-nitro form should get deprotonated by NaOH. I know NU is more vulnerable to alkaline hydrolysis than NQ, but is the difference so great that yields are abysmal even with a short reaction time?

[Edited on 23-4-2024 by Yorty2040]
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