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UBC Theses and Dissertations

Deuterium isotope effects in organic cations Mocek, Michael M.


The effect of ⍺ -deuterium substitution upon the ionisation of five identically di-substituted benzhydrols was studied. It was found that the equilibrium isotope effect KH/KD, which varied from 1.03 to 1.35, was small if the substituents were basic in character but was greater in the case of substituents with electron withdrawing properties. The ionisation of Michler's Hydrol was quantitatively examined at acidities up to 30% fuming sulfuric acid, and upon the spectral and other evidence, the existence of two new carbonium ions is postulated. The isotope effect was also determined for the above entities and it was found that the effect increases with the number of protonated nitrogens. The effect of five solvents upon the ionisation of Michler's Hydrol Blue was examined and a conclusion was reached that the carbonium ion is almost completely ionised in some of these solvents.

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