A kinetic study of the hydrogen abstraction reactions from tetrahydrofuran (THF) and cyclohexane (CHX) by the cumyloxyl radical was carried out in different solvents. With THF, a 4.5-fold decrease in rate constant (kH) was observed on going from isooctane to 2,2,2-trifluoroethanol. An opposite behavior was observed with CHX, where kH increased by a factor 4 on going from isooctane to 2,2,2-trifluoroethanol. The important role of substrate structure and of the solvent hydrogen bond donor ability is discussed.
Bietti, M., Martella, R., Salamone, M. (2011). Understanding Kinetic Solvent Effects on Hydrogen Abstraction Reactions from Carbon by the Cumyloxyl Radical. ORGANIC LETTERS, 13(22), 6110-6113 [10.1021/ol202561z].
Understanding Kinetic Solvent Effects on Hydrogen Abstraction Reactions from Carbon by the Cumyloxyl Radical
BIETTI, MASSIMO;SALAMONE, MICHELA
2011-10-25
Abstract
A kinetic study of the hydrogen abstraction reactions from tetrahydrofuran (THF) and cyclohexane (CHX) by the cumyloxyl radical was carried out in different solvents. With THF, a 4.5-fold decrease in rate constant (kH) was observed on going from isooctane to 2,2,2-trifluoroethanol. An opposite behavior was observed with CHX, where kH increased by a factor 4 on going from isooctane to 2,2,2-trifluoroethanol. The important role of substrate structure and of the solvent hydrogen bond donor ability is discussed.| File | Dimensione | Formato | |
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