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.
Journal of the Chemical Society, Perkin Transactions 2, no. 9 (2001): 1631–1633.