| |  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 |
|---|
| |
|
|---|
| | |
|---|
| Lokale URL UB: |  Zum Volltext |
|---|
¬An¬ air-stable, neutral phenothiazinyl radical with substantial radical stabilization energy / Sigmund, Lukas M. [VerfasserIn]; 2020 (Online-Ressource)
