N-H stretch region IR spectroscopy has been used to probe the hydrogen bond-donating properties of six structurally related secondary amides in which the amide group is flanked by sterically bulky groups. For three of the compounds, solid state IR analysis reveals N-R stretch bands >3400 cm(-1), which suggests the absence of intermolecular N-H-O=C hydrogen bonds. Crystallographic data for these three amides confirm the absence of a standard N-H-O=C interaction. For the other three amides, N-H stretch bands in the range 3370-3290 cm(-1) suggest the occurrence of intermolecular N-H-O=C hydrogen bonds in the solid state, but high quality crystals could not be grown. Steric hindrance to hydrogen bond donation by these amides is manifested in IR data obtained in DMSO: although this solvent is a strong hydrogen bond acceptor, N-H stretch bands are observed for both solvent-hydrogen bonded and non-hydrogen bonded amide groups. The amides described here and related compounds should be useful for calibrating spectroscopic methods that are intended to detect hydrogen bond formation.