Electron transfer chemistry of some unusual nitrogen compounds: From stable nitrenium ions to the corresponding nitrogen centered radicals

Marc Robert, Andreas Neudeck, Gernot Boche, Christoph Willeke, Kanchugarakoppal S. Rangappa, Phil Andrews

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Nitrogen-centered radicals (1b., 2b., 3b., 4b.) have been generated upon electron transfer from the corresponding stable nitrenium ions (1b+, 2b+, 3b+, 4b+) and characterized by electrochemistry and simultaneous spectro-electrochemistry. Reactivity of the radicals is strongly influenced by the substituents attached to the two nitrogen atoms that are directly linked to the ion nitrenium center. While 1b. and 2b. are stable on the timescale of the electrochemical experiment, 3b. and 4b. have half-lifetimes of ca. 1.2-1.25 and 0.9-1 μs, respectively, in acetonitrile, as determined with ultramicroelectrodes. Redox properties of the nitrenium ion/radical couples and relative stability of the radicals are discussed in light of both experimental results and ab initio calculations.

Original languageEnglish
Pages (from-to)1437-1444
Number of pages8
JournalNew Journal of Chemistry
Issue number12
Publication statusPublished - 1 Jan 1998
Externally publishedYes

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