Abstract
The relative effectiveness of intramolecular nucleophilic and general acid catalysis are compared in the hydroxide-ion catalysed hydrolysis of N-(2-amino-ethyl)-2-endo-hydroxy-6-endo-norbornamide in its amino protonated form; the rate enhancement of ca. 109 is due mainly to nucleophilic catalysis by the neighbouring hydroxy group with only a relatively minor contribution from the protonated amino group acting as a general acid.
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