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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 A1HA2. 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.

Energetics and cooperativity in three-center hydrogen bonding interactions. II. Intramolecular hydrogen bonding systems