Journal of Organic Chemistry p. 192 - 196 (1993)
Update date:2022-08-16
Topics:
Kim, Sung Soo
Kim, Sung Yeon
Ryou, Seung Sin
Lee, Choon Seung
Yoo, Kwang Hee
The Hammett correlations and primary deuterium kinetic isotope effects were obtained to investigate the solvent effects on hydrogen abstractions from thiophenols, phenols, and toluenes by tert-butoxy radical, where the latter proved to be a more sensitive probe than the former.The limitations of the reactivity/selectivity principle are discussed in terms of either anti-Hammond effects or Marcus theory and attributed to the duality in substituent (solvent) effects.While the polar transition states for the homolytic reactions should invite dual substituent effects, the dual solvations of tert-butoxy radical could trigger the dualism of solvent effects.The influence on the rates in general may dwindle in the order of structure > substituent > solvent.
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