Protonation of CH3N3 and CF3N3 in Superacids: Isolation and Structural Characterization of Long‐Lived Methyl‐ and Trifluoromethylamino Diazonium Ions
The result's identifiers
Result code in 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>
Alternative codes found
RIV/00216208:11310/20:10421737
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Protonation of CH3N3 and CF3N3 in Superacids: Isolation and Structural Characterization of Long‐Lived Methyl‐ and Trifluoromethylamino Diazonium Ions
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/LTAUSA18037" target="_blank" >LTAUSA18037: Synthesis and reactivity of N-fluoroalkylated compounds</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Angewandte Chemie - International Edition
ISSN
1433-7851
e-ISSN
—
Volume of the periodical
59
Issue of the periodical within the volume
30
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
12520-12526
UT code for WoS article
000537460600001
EID of the result in the Scopus database
2-s2.0-85085982851