Sciencemadness Discussion Board

What is 1,3-diisonitrosoacetone guanidinium salt

iamben250 - 11-9-2010 at 23:20

I googled it but only found 1,3-diisonitrosoacetone。
I want to know the structure and details.
thanks to those give me a hand.

iamben250 - 12-9-2010 at 00:10

I finally got the method to prepare the salt.
Sass, S., W. D. Ludemann, et al. (1957). "COLORIMETRIC DETERMINATION OF CERTAIN ORGANOPHOSPHORUS COMPOUNDS AND ACYLATING AGENTS - USE OF DIISONITROSOACETONE REAGENT." ANALYTICAL CHEMISTRY 29(9): 1346-1349.
brief details：
Reaction of guanidine and 1,3-diisonitrosoacetone easily forms the salt.


now I have a new question:
how to get pure guanidine, the commercial product of it nomally is its salt.
who help tell me how to carry out the reaction between guanidine and 1,3-diisonitrosoacetone?
thanks.

[Edited on 12-9-2010 by iamben250]

DDTea - 12-9-2010 at 00:16

Even dumb, small animals like rodents keep their shit in one spot...but since you're tracking your guano everywhere you go, let's just address this so you'll stop. Then, some nice moderator may come and pick this up and throw it into "detritus."

If you can use google, you can look up what a guanidine is. Guanidine forms a cation. So, look up "guanidinium cation."

The molecule you speak of is a salt: 1,3-diisonitrosoacetone + guanidinium.

iamben250 - 12-9-2010 at 00:32

Quote: Originally posted by DDTea  
Even dumb, small animals like rodents keep their shit in one spot...but since you're tracking your guano everywhere you go, let's just address this so you'll stop. Then, some nice moderator may come and pick this up and throw it into "detritus."

If you can use google, you can look up what a guanidine is. Guanidine forms a cation. So, look up "guanidinium cation."

The molecule you speak of is a salt: 1,3-diisonitrosoacetone + guanidinium.


Rodent can't post the post, nor post as you.
Thank you all the way.
What a pity that making you with me ”detritus“ .

however
Do you know how to resolve the latter question with commercial chemicals?

Anders2 - 15-9-2010 at 18:08

diisonitrosoacetone can condense with hydroxylamine to form
1,2-dinitroso-propyl,2-oxime.

It is called "nitroso" because that is the demoninant tautomer at neutral conditions.
Making it basic, the oxime tautomer dominates, and this is what can act as an acid.
O=NCH2C(=O)CH2N=O and HON=CHC(=O)CH=NOH

1,2-dinitroso-propyl,2-oxime can act like a triple acid, forming salts with the -3 anion,
(-)ON=CHC(=NO(-))CH=NO(-)

1,2-dinitroso-propyl,2-oxime could either be reduced with bisulfite to give a decent yield of propyl trihydroxylamine, or oxidized with NO2 bubbled in to form real "nitroglycerin", with 3 nitro groups instead of nitrate.

kmno4 - 17-9-2010 at 15:03

Quote: Originally posted by Anders2  
diisonitrosoacetone can condense with hydroxylamine to form
1,2-dinitroso-propyl,2-oxime.

It is called "nitroso" because that is the demoninant tautomer at neutral conditions.

Aliphatic nitroso compounds with alpha-hydrogen(s) very quickly rearrange to stable oximato(=isonitroso) form, so nitroso forms are not stabe tautomers.
Diisonitrosoacetone gives trioxime derivative upon treatment with hydroxylamine.

Anders2 - 17-9-2010 at 15:15

"results indicate that the rearrangement from nitrosomethane to more stable trans-formaldoxime" , EXPLORING THE POTENTIAL ENERGY SURFACE OF THE CATALYZED ISOMERIZATION OF NITROSOMETHANE TO FORMALDOXIME by GUO-MING LIANG

from a patent: "The trimer is a high melting solid (MP145.-156.degree. C)

In the reaction in water, there apparently exists an equilibrium between the trimer and monomer. The formaldoxime monomer stays as the monomer in dilute solution but when formaldoxime monomer reaches 15-20 weight percent, the trimer will start to form. The rate and extent of the trimer formation seem to depend on temperature/pH/time. The higher the pH, the more the amount of monomer which forms."

iamben250 - 10-1-2011 at 05:30

Quote: Originally posted by Anders2  
diisonitrosoacetone can condense with hydroxylamine to form
1,2-dinitroso-propyl,2-oxime.

It is called "nitroso" because that is the demoninant tautomer at neutral conditions.
Making it basic, the oxime tautomer dominates, and this is what can act as an acid.
O=NCH2C(=O)CH2N=O and HON=CHC(=O)CH=NOH

1,2-dinitroso-propyl,2-oxime can act like a triple acid, forming salts with the -3 anion,
(-)ON=CHC(=NO(-))CH=NO(-)

1,2-dinitroso-propyl,2-oxime could either be reduced with bisulfite to give a decent yield of propyl trihydroxylamine, or oxidized with NO2 bubbled in to form real "nitroglycerin", with 3 nitro groups instead of nitrate.

thanks. much helpful.

madscientist - 10-1-2011 at 07:24

Don't take what he said at face value. Notice he is banned - he was a prolific poster of unverified information, which sometimes proved to be outright dangerous and wrong.

Nicodem - 10-1-2011 at 10:59

By the rule of thumb: If someone posts so much specific information about a narrow case and doesn't provide any reference, chances are huge that it is all just bullshit.