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The rate of the initial protonation of 3 is significantly slower than any of the other models, but 3 is very rapidly protonated at the nitrogen atom. This means that the bridge protonation is occurring on an already charged species rather than the neutral compound.
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23
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85163246131
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1H NMR spectroscopy.
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85163245233
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note
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1H} NMR spectrum for 4 shows a single peak at δ = 21.79 ppm. On cooling to -60°C, this splits into broad signals at δ = 19.90 and 27.12 ppm and a sharp signal at δ = 28.34 ppm, demonstrating that more than one isomer is present in solution.
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