Magnetic Nonequivalence in the Low-Temperature Nuclear Magnetic Resonance Spectra of N-benzyl-N-Methylhydroxylamine and N-Benzyl-N-methylchloramine

Reinvestigation of the low-temperature nmr spectra of N-benzyl-N-methylhydroxylamine and N-benzyl-N-methylchloramine in acetone-d_6 at 100 MHz has revealed magnetic nonequivalence. The slow process with the N-chloro compound must be nitrogen inversion. The fact that, in acetone-d_6 N-benzyl-N-methylhydroxylamine undergoes degenerate racemization more slowly than N-benzyl-O,N-dimethylhydroxylamine supports the hypothesis that inversion of nitrogen is slower than the rate of rotation about the N-O bond in these compounds.