An air-stable, neutral phenothiazinyl radical with substantial radical stabilization energy
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,...
Gespeichert in:
| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2020
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| In: |
Chemistry - a European journal
Year: 2020, Jahrgang: 26, Heft: 14, Pages: 3152-3156 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201905238 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.201905238 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201905238 
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| Verfasserangaben: | Lukas M. Sigmund, Fabian Ebner, Christoph Jöst, Jonas Spengler, Nils Gönnheimer, Deborah Hartmann, and Lutz Greb |
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| 245 | 1 | 3 | |a An air-stable, neutral phenothiazinyl radical with substantial radical stabilization energy |c Lukas M. Sigmund, Fabian Ebner, Christoph Jöst, Jonas Spengler, Nils Gönnheimer, Deborah Hartmann, and Lutz Greb |
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| 520 | |a 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. | ||
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