Protonation of CH3N3 and CF3N3 in Superacids: Isolation and Structural Characterization of Long‐Lived Methyl‐ and Trifluoromethylamino Diazonium Ions
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00525622" target="_blank" >RIV/61388963:_____/20:00525622 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/00216208:11310/20:10421737
Výsledek na webu
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202002750" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202002750</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.202002750" target="_blank" >10.1002/anie.202002750</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Protonation of CH3N3 and CF3N3 in Superacids: Isolation and Structural Characterization of Long‐Lived Methyl‐ and Trifluoromethylamino Diazonium Ions
Popis výsledku v původním jazyce
The methylamino diazonium cations [CH3N(H)N-2](+) and [CF3N(H)N-2](+) were prepared as their low-temperature stable [AsF6](-) salts by protonation of azidomethane and azidotrifluoromethane in superacidic systems. They were characterized by NMR and Raman spectroscopy. Unequivocal proof of the protonation site was obtained by the crystal structures of both salts, confirming the formation of alkylamino diazonium ions. The Lewis adducts CH3N3.AsF5 and CF3N3.AsF5 were also prepared and characterized by low-temperature NMR and Raman spectroscopy, and also by X-ray structure determination for CH3N3.AsF5. Electronic structure calculations were performed to provide additional insights. Attempted electrophilic amination of aromatics such as benzene and toluene with methyl- and trifluoromethylamino diazonium ions were unsuccessful.
Název v anglickém jazyce
Protonation of CH3N3 and CF3N3 in Superacids: Isolation and Structural Characterization of Long‐Lived Methyl‐ and Trifluoromethylamino Diazonium Ions
Popis výsledku anglicky
The methylamino diazonium cations [CH3N(H)N-2](+) and [CF3N(H)N-2](+) were prepared as their low-temperature stable [AsF6](-) salts by protonation of azidomethane and azidotrifluoromethane in superacidic systems. They were characterized by NMR and Raman spectroscopy. Unequivocal proof of the protonation site was obtained by the crystal structures of both salts, confirming the formation of alkylamino diazonium ions. The Lewis adducts CH3N3.AsF5 and CF3N3.AsF5 were also prepared and characterized by low-temperature NMR and Raman spectroscopy, and also by X-ray structure determination for CH3N3.AsF5. Electronic structure calculations were performed to provide additional insights. Attempted electrophilic amination of aromatics such as benzene and toluene with methyl- and trifluoromethylamino diazonium ions were unsuccessful.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/LTAUSA18037" target="_blank" >LTAUSA18037: Syntéza a reaktivita N-fluoralkylovaných sloučenin</a><br>
Návaznosti
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2020
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Angewandte Chemie - International Edition
ISSN
1433-7851
e-ISSN
—
Svazek periodika
59
Číslo periodika v rámci svazku
30
Stát vydavatele periodika
DE - Spolková republika Německo
Počet stran výsledku
7
Strana od-do
12520-12526
Kód UT WoS článku
000537460600001
EID výsledku v databázi Scopus
2-s2.0-85085982851