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Verfasst von:Sigmund, Lukas M. [VerfasserIn]   i
 Ebner, Fabian [VerfasserIn]   i
 Jöst, Christoph [VerfasserIn]   i
 Spengler, Jonas [VerfasserIn]   i
 Gönnheimer, Nils [VerfasserIn]   i
 Hartmann, Deborah [VerfasserIn]   i
 Greb, Lutz [VerfasserIn]   i
Titel:An air-stable, neutral phenothiazinyl radical with substantial radical stabilization energy
Verf.angabe:Lukas M. Sigmund, Fabian Ebner, Christoph Jöst, Jonas Spengler, Nils Gönnheimer, Deborah Hartmann, and Lutz Greb
Jahr:2020
Umfang:5 S.
Fussnoten:First published: 16 January 2020 ; Gesehen am 22.11.2021
Titel Quelle:Enthalten in: Chemistry - a European journal
Ort Quelle:Weinheim : Wiley-VCH, 1995
Jahr Quelle:2020
Band/Heft Quelle:26(2020), 14, Seite 3152-3156
ISSN Quelle:1521-3765
Abstract:The vital effect of radical states on the pharmacological activity of phenothiazine-based drugs has long been speculated. Whereas cationic radicals of N-substituted phenothiazines show high stability, the respective neutral radicals of N-unsubstituted phenothiazines have never been isolated. Herein, the 1,9-diamino-3,7-di-tert-butyl-N1,N9-bis(2,6-diisopropylphenyl)-10H-phenothiazin-10-yl radical (SQH2.) is described as the first air-stable, neutral phenothiazinyl free radical. The crystalline dark-blue species is characterized by means of EPR and UV/Vis/near-IR spectroscopy, as well as cyclic voltammetry, spectro-electrochemical analysis, single-crystal XRD, and computational studies. The SQH2. radical stands out from other aminyl radicals by an impressive radical stabilization energy and its parent amine has one of the weakest N−H bond dissociation energies ever determined. In addition to serving as open-shell reference in medicinal chemistry, its tridentate binding pocket or hydrogen-bond-donor ability might enable manifold uses as a redox-active ligand or proton-coupled electron-transfer reagent.
DOI:doi:10.1002/chem.201905238
URL:kostenfrei: Volltext ; Verlag: https://doi.org/10.1002/chem.201905238
 kostenfrei: Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201905238
 DOI: https://doi.org/10.1002/chem.201905238
Datenträger:Online-Ressource
Sprache:eng
Sach-SW:aminyl radicals
 phenothiazines
 radical stabilization energy
 radicals
 redox chemistry
K10plus-PPN:1778268366
Verknüpfungen:→ Zeitschrift
 
 
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