Nuclear Magnetic Resonance Spectroscopy. Slow Nitrogen Inversion in an Acyclic Substituted Hydrazine

Changes which were found to occur in the proton nmr spectrum of benzyltrimethylhydrazine at low temperatures are discussed in terms of hindered rotation about the nitrogen-nitrogen bond and slow nitrogen inversion. It is concluded that, below -130°, inversion of the nitrogen atom bearing the benzyl group is slow on the nmr time scale. The barrier to inversion is calculated to be 6.8 kcal/mol, which is substantially lower than the barriers found for cyclic and bicyclic hydrazines or for group V analogs of hydrazine.