Revision of the α2 H value for N,N-dialkylhydroxylamines based on kinetic and spectroscopic measurements

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DOIResolve DOI: http://doi.org/10.1039/B102247O 
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TypeArticle
Journal titleJournal of the Chemical Society, Perkin Transactions 2
ISSN1470-1820
Issue9
Pages16311633; # of pages: 3
SubjectComputational methods; Hydrogen bonds; Infrared spectroscopy; Reaction kinetics; Solvents; Hydrogen-atom abstraction; Kinetic solvents; Amines
AbstractKinetic solvent effects on hydrogen-atom abstraction from N,N-diethylhydroxylamine and N,N-dibenzylhydroxylamine by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH·) indicated that these compounds are much weaker hydrogen-bond donors than implied by the currently accepted α2 H value of 0.453. Lower α2 H values were also obtained by monitoring 1 : 1 complex formation with two strong hydrogen-bond acceptors, HMPA and DMSO, in tetrachloromethane using IR spectroscopy. It is concluded that the α2 H value for sterically non-hindered N,N-dialkylhydroxylamines should be revised downward to 0.29.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276577
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Record identifier86b5b975-9f6b-40b4-8928-73ee552b4495
Record created2015-10-13
Record modified2016-05-09
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