期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 1, 页码 249-263出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202839
关键词
carbocations; hydride transfer; kinetics; linear free energy relationships; reactivity parameters
资金
- Deutsche Forschungsgemeinschaft [SFB 749]
- Fonds der Chemischen Industrie (Liebig-Stipendium)
Rates of hydride transfer from several hydride donors to benzhydrylium ions have been measured at 20 degrees C and used for the determination of empirical nucleophilicity parameters N and s(N) according to the linear free energy relationship logk(20 degrees C)=s(N)(N+E). Comparison of the rate constants of hydride abstraction by tritylium ions with those calculated from the reactivity parameters s(N), N, and E showed fair agreement. Therefore, it was possible to convert the large number of literature data on hydride abstraction by tritylium ions into N and s(N) parameters for the corresponding hydride donors, and construct a reactivity scale for hydride donors covering more than 20 orders of magnitude.
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