Rate constants for nitrogen inversion in N-benzyl-N-methylhydroxylamine, NJV- diethylhydroxylamine, 1-hydroxy-2, 2, 4, 4-tetramethylpyrrolidine, their conjugate bases, and their 0-acetyl derivativea in dimethylformamide-d, were determined based on the'H NMR coalescence temperatures. Relative to-OH, the-0- substituent ought to either raise the barrier to inversion owing to stronger lone-pair repulsions or lower the barrier owing to weaker u- ...
