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Photo- and radiation-chemical formation and electrophilic and electron transfer reactivities of enolether radical cations in aqueous solution

In aqueous solution, enolether radical cations (EE.+) were generated by photoionization (?≤222 nm) or by electron transfer to radiation-chemically produced oxidizing radicals. Like other radical cations, the EE.+ exhibit electrophilic reactivity with respect to nucleophiles such as water or phosphat...

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Hauptverfasser: Bernhard, Klaus (VerfasserIn) , Geimer, Judith (VerfasserIn) , Canle-Lopez, Moises (VerfasserIn) , Reynisson, Johannes (VerfasserIn) , Beckert, Dieter (VerfasserIn) , Gleiter, Rolf (VerfasserIn) , Steenken, Steen (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 30 October 2001
In: Chemistry - a European journal
Year: 2001, Jahrgang: 7, Heft: 21, Pages: 4640-4650
ISSN:1521-3765
DOI:10.1002/1521-3765(20011105)7:21<4640::AID-CHEM4640>3.0.CO;2-E
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/1521-3765(20011105)7:21<4640::AID-CHEM4640>3.0.CO;2-E
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/1521-3765%2820011105%297%3A21%3C4640%3A%3AAID-CHEM4640%3E3.0.CO%3B2-E
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Verfasserangaben:Klaus Bernhard, Judith Geimer, Moises Canle-Lopez, Johannes Reynisson, Dieter Beckert, Rolf Gleiter, and Steen Steenken
Beschreibung
Zusammenfassung:In aqueous solution, enolether radical cations (EE.+) were generated by photoionization (?≤222 nm) or by electron transfer to radiation-chemically produced oxidizing radicals. Like other radical cations, the EE.+ exhibit electrophilic reactivity with respect to nucleophiles such as water or phosphate as well as electron transfer reactivity, for example, towards one-electron reductants such as phenols, amines, vitamins C and E, and guanine nucleosides. The reactivity of these electron donors with the radical cation of cis-1,2-dimethoxyethene.+ (DME.+) can be described by the Marcus equation with the reorganization energy ?=16.5 kcal?mol?1. By equilibrating DME.+ with the redox standard 1,2,4-trimethoxybenzene, the reduction potential of DME.+ is determined to be 1.08±0.02 V/NHE. The oxidizing power of the radical cation of 2,3-dihydrofuran, which can be considered a model for the enolether formed on strand breakage of DNA, is estimated to be in the range 1.27?1.44 V/NHE.
Beschreibung:Gesehen am 22.10.2020
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/1521-3765(20011105)7:21<4640::AID-CHEM4640>3.0.CO;2-E

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