Intermolecular hydrogen bonding modulates the hydrogen-atom donating ability of hydroquinones

被引:20
作者
Amorati, Riccardo [1 ]
Franchi, Paola [1 ]
Pedulli, Gian Franco [1 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy
关键词
EPR spectroscopy; hydrogen bonds; hydrogen transfer; quinones; radical reactions;
D O I
10.1002/anie.200701957
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Radical measures: Kinetic measurements on peroxyl radicals showed that the reactivity of a 1,4-dihydroxybenzene is enhanced by the selective interaction of one OH group with a cosolvent molecule (see scheme; S = DMSO, 2.3 mn). The preferential solvation of the radical over the parent phenol causes a decrease in the bond dissociation enthalpy of the free OH group and an increase in the rate constant for abstraction of a hydrogen atom. (Chemical Equation Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6336 / 6338
页数:3
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