Lotilko
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Azidohydrazine
I stumbled across an interesting compound while I was browsing today: https://pubchem.ncbi.nlm.nih.gov/compound/3033846
I was doubtful of it's existence until a search revealed a few suppliers.
I UTFSE but I couldn't find any valuable information on this compound. I don't request spoonfeeding, but since I wasn't able to find any resources,
could any of you provide some useful information like stability, MP, BP, a synthesis route and energetic properties? And also, while we're at it,
would it be suitable in ring closure reactions to produce N-hydrazinotetrazole derivatives?
Greatly appreciated.
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LiBr
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I found a little blurb about it on wikipedia https://en.wikipedia.org/wiki/Hydrazinium which had some articles cited underneath.
[Edited on 25-9-2016 by LiBr]
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camerican
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I couldn't find anything Hydrazinium Azide itself, but there were some .pdfs floating around which described the synthesis of some derivatives. These
articles mentioned some of its properties in their abstracts. All the work I found was performed by Anton Hammerl. Hope this helps!
Attachment: Hydrazinium Azide Hydrazinate.pdf (85kB)
This file has been downloaded 527 times
Attachment: Hydrazinium Azide Compounds.pdf (151kB)
This file has been downloaded 458 times
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Lotilko
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Thank you very much camerican and LiBr!
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kratomiter
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Regarding to the Hydrazinium Azide Compounds attachment: could the reaction of DNPH with NH3 in ether give dinitrophenylhydrazinium azide
dinitrophenylhydrazinate?
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PHILOU Zrealone
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Quote: Originally posted by kratomiter  | | Regarding to the Hydrazinium Azide Compounds attachment: could the reaction of DNPH with NH3 in ether give dinitrophenylhydrazinium azide
dinitrophenylhydrazinate? |
In principle the NH (between the aromatic ring (holding two NO2) and the terminal NH2) is more acidic/less basic.
So there is indeed a chance it allows for a NH4(+) salt or even a N2H5(+) one.
H2N-NH-C6H3(NO2)2 + NH3 <---> H2N-N(NH4)-C6H3(NO2)2
H2N-NH-C6H3(NO2)2 + H2N-NH2 <---> H2N-N(N2H5)-C6H3(NO2)2
Would be better to use TNPH (trinitrophenylhydrazine) to get a for sure acidic compound and thus favour the formation of aminium salts.
H2N-NH-C6H2(NO2)3 + NH3 ---> H2N-N(NH4)-C6H2(NO2)3
H2N-NH-C6H2(NO2)3 + H2N-NH2 ---> H2N-N(N2H5)-C6H2(NO2)3
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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PHILOU Zrealone
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| Quote: Originally posted by PHILOU Zrealone | | Quote: Originally posted by kratomiter | | Regarding to the Hydrazinium Azide Compounds attachment: could the reaction of DNPH with NH3 in ether give dinitrophenylhydrazinium azide
dinitrophenylhydrazinate? |
In principle the NH (between the aromatic ring (holding two NO2) and the terminal NH2) is more acidic/less basic.
So there is indeed a chance it allows for a NH4(+) salt or even a N2H5(+) one.
H2N-NH-C6H3(NO2)2 + NH3 <---> H2N-N(NH4)-C6H3(NO2)2
H2N-NH-C6H3(NO2)2 + H2N-NH2 <---> H2N-N(N2H5)-C6H3(NO2)2
Would be better to use TNPH (trinitrophenylhydrazine) to get a for sure acidic compound and thus favour the formation of aminium salts.
H2N-NH-C6H2(NO2)3 + NH3 ---> H2N-N(NH4)-C6H2(NO2)3
H2N-NH-C6H2(NO2)3 + H2N-NH2 ---> H2N-N(N2H5)-C6H2(NO2)3 |
Sorry I missed the point of your question...
Without azide present into the reaction...no azide will be formed from aromatic hydrazine and NH3.
The reaction of DNPH (dinitrophenylhydrazine) and NH4N3 is following me excluded as it would probably lead to:
H2N-NH-C6H2(NO2)3 + NH4N3 ---> H2N-N(NH4)-C6H2(NO2)3 + HN3
HN3 is explosive, volatile and also very toxic (like HCN (cyanhydric acid)).
Maybe if the terminal NH2 is basic enough and if the NH is not too acidic that you may form an azide salt:
H2N-NH-C6H3(NO2)2 + HN3 ---> N3H3N-NH-C6H3(NO2)2
But more likely the DNPH will display a zwiterionic behaviour:
H2N-NH-C6H3(NO2)2 ---> H3N(+)-N(-)-C6H3(NO2)2
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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kratomiter
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Thank you PHILOU!
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