Model peptides 1-6 are prepared and studied by IR and variable temperature H-1 NMR spectroscopies. The alpha-hydroxy diamides 3 and 4 form intramolecular amide-amide hydrogen bond through an eight-membered and a nine-membered ring, respectively. When compared to Gellman's simple diamides of same chain length, the enhanced hydrogen bond strength is considered as an indication of a cooperative effect.