Proton exchange and hydrogen bonding in hydroxylamine derivatives

Proton exchange in hydroxylamines, RNHOH, has been investigated by nuclear magnetic resonance spectroscopy. Hydrogen bonding of the hydroxylamines and their N,N-and N,O-disubstituted derivatives by self-association as well as by their interaction with electron donors has been studied by nuclear magnetic resonance and infrared spectroscopy. The results indicate that the OH group participates to a greater extent in hydrogen bonding than the NH group. The O-H⋯Y (Y = donor site) hydrogen bonds are found to be generally stronger than the N-H⋯Y bonds.