| Online-Ressource |
Verfasst von: | Sigmund, Lukas M. [VerfasserIn]  |
| Ebner, Fabian [VerfasserIn]  |
| Jöst, Christoph [VerfasserIn]  |
| Spengler, Jonas [VerfasserIn]  |
| Gönnheimer, Nils [VerfasserIn]  |
| Hartmann, Deborah [VerfasserIn]  |
| Greb, Lutz [VerfasserIn]  |
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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Lokale URL UB: | Zum Volltext |
¬An¬ air-stable, neutral phenothiazinyl radical with substantial radical stabilization energy / Sigmund, Lukas M. [VerfasserIn]; 2020 (Online-Ressource)