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

DOI	Resolve DOI: https://doi.org/10.1039/B102247O
Author	Search for: Astolfi, P.; Search for: Greci, L.; Search for: Paul, T.; Search for: Ingold, K. U.¹
Name affiliation	National Research Council of Canada
Format	Text, Article
Subject	Computational methods; Hydrogen bonds; Infrared spectroscopy; Reaction kinetics; Solvents; Hydrogen-atom abstraction; Kinetic solvents; Amines
Abstract	Kinetic 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	2001
In	Journal of the Chemical Society, Perkin Transactions 2, no. 9 (2001): 1631–1633.
Language	English
Peer reviewed	Yes
NPARC number	21276577
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Record identifier	86b5b975-9f6b-40b4-8928-73ee552b4495
Record created	2015-10-13
Record modified	2020-03-27