Calorimetric and equilibrium studies on some stable nitroxide and iminoxy radicals. Approximate O-H bond dissociation energies in hydroxylamines and oximes

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DOIResolve DOI: http://doi.org/10.1021/ja00807a018
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume95
Issue26
Pages86108614; # of pages: 5
AbstractThe differences in the heats of formation in solution of the stable free radicals, 2,2,6,6-tetramethylpiperid-4-one 1-oxyl (1a), 2,2,6,6-tetramethylpiperdine N-oxyl (1b), and di-tert-butyliminoxy (2), and their hydrogenated precursors have been determined by a direct calorimetric technique. The equilibrium constants for the hydrogen atom transfer reactions of these radicals with certain hydroxylamines and oximes were then determined by the epr spectroscopic method. The analysis of the results of these experiments leads to the predictions that the O-H bond strengths of unhindered dialkylhydroxylamines are in the range of 72-74 kcal/mol while the O-H bond strengths of simple unhindered oximes are equal to approximately 86 kcal/mol.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276781
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Record identifier297e2c22-f57f-4b7b-be37-ba7646e8c982
Record created2015-10-13
Record modified2016-05-09
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