Mannich bases as model compounds for intramolecular hydrogen bonding .1. Solid state structures and molecular calculations

A survey of the structures and the properties of the hydrogen bonds in ortho-aminomethyl-phenols and -naphthols in the solid state is presented. The results are compared with molecular structure calculations. The solid state complexes can exist in the molecular or in zwitterionic form. In the last case, only intermolecular hydrogen bonds forming cyclic dimers or linear chains were detected.