High level ab initio calculations have been carried out on a number of intramolecular two- and three-center H-bonding structures containing the amide motif, NHC=O. These structures serve as model systems for probing the stability of intramolecular three-center H bonds of the type A(1)HA(2). Particular attention is given to cooperative effects in the three-center H-bonding structures. A systematic assessment of cooperativity for intramolecular H-bonding systems is presented.