Abstract
Non-equivalence of the benzylic hydrogens was found in several N-phenyl-ortho-hydroxybenzyl-amines and, where possible, activation parameters were calculated for the processes causing non-equivalence. Hindered rotation about the aromatic carbon-nitrogen bond was the rate determining process with an ortho-t-butyl group on the aniline ring. Exchange of phenolic and amino hydrogens was studied over a range of temperature and concentration. Both intermolecular and intramolecular exchange were observed. The latter may be the first example of such a process to be studied by n.m.r.
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