A systematic investigation of carbamate stability constants by 1H NMR

A systematic, experimental investigation into carbamate stability constants using 1H NMR spectroscopy reveals that both steric hindrance and the acid dissociation constant of the parent amine have a significant effect on the stability of the resulting carbamates. Increasing steric hindrance was found to decrease carbamate stability, while increasing pK of the parent amine was found to increase carbamate stability. The carbamate stability constants of monoethanolamine, propylamine, isobutylamine, 2-amino-1-propanol, aminomethylpropanol and methyldiethanolamine were determined as were the carbamate protonation constants of the first four of these amines.