Hydrogen donor ability

Note, Added in Proof-. In their study of the autoxidation of 2-butyl-isoindoline, Kochi and Singleton showed that 2-butylisoindole is formed and is converted by further oxidation to 2-butylphthalimide and 2-butylphthalimidine. The rate of oxidation of 2-butylisoindoline to the isoindole was found to be markedly dependent on hydrogen donor ability of the solvent and was shoivn to involve a free radical chain process. Autoxidation of 2-butylisoindole also appears to be a radical process since it can initiate autoxidation of 2-butylisoindoline. 

Chatgilialoglu, Chryssostomos, and Newcomb, Martin, Hydrogen Donor Abilities... 

The hydrogen-donor ability of germanium hydrides has been studied123 and reviewed.124... 

I thank Keith U. Ingold for having introduced me to this subject. When I arrived in Ottawa at the National Research Council of Canada in 1979 for three years postdoctoral work with him, very little was known on the reactivity of silyl radicals. At that time, several papers dealing with kinetics of silyl radicals were published, which allowed the reactivity of silyl radical to be translated into a quantitative base. Special thanks go to David Griller for his collaboration on the initial work on hydrogen donor abilities of silicon hydrides during the late 1980s. 

As far as the use of silanes as mediators in consecutive radical reactions is concerned, the knowledge of their hydrogen donor abilities coupled with the steric hindrance given by the silicon substituents has contributed substantially in this area, with interesting results in terms of reactivity and stereoselectivity. 

C. Chatgihaloglu and M. Newcomb, Hydrogen donor abilities of the group 14 hydrides, Adv. Organometal Chem. 1999, 44, 67 (rate constants for radical reactions with Group 14 (IV A) metal hydrides). 

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