N-tert-butoxy-N-tert-alkylaminyls. A new class of persistent radicals

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DOIResolve DOI: http://doi.org/10.1021/ja00531a024
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume102
Issue11
Pages38133815; # of pages: 3
AbstractN-tert-Butoxy-N-tert-butylaminyl (1•) and three related radicals have been generated from their parent hydroxylamines in hydrocarbon solution. In the absence of oxygen these radicals are extremely persistent. Their electronic structures, as indicated by their EPR parameters (a14N, a17O, and a13C, all determined without isotopic enrichment) and the N-H bond strength in 1-H (measured as 81.0 kcal/mol), show that the effectiveness of conjugative electron delocalization is reduced relative to that in the isomeric nitroxides. This effect is attributed to the greater electronegativity of oxygen compared with nitrogen. © 1980 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276649
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Record identifier6bc6fd20-d809-4346-a890-0c0a5ac2c0eb
Record created2015-10-13
Record modified2016-05-09
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