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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

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • 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