Abstract
Gas-phase proton transfer from benzyl alcohol to fluoride ion is encounter controlled, whereas transfer from neopentyl alcohol to fluoride ion is slow. These observations suggest that the equilibrium gas-phase acidity of HF lies between those of the two alcohols, in contrast to the tabulated order. A small adjustment in the gas-phase acidities of alcohols not only makes the kinetics consistent but also resolves a long-standing discrepancy between RO-H bond energies measured by kinetic techniques and those determined by acidity/electron affinity data. It also accounts for the observed branching ratio in the IR laser photolysis of the neopentyl alcohol-fluoride ion complex. 21 references, 1 table.
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