Molecular orbital and density functional theory calculations are performed on some di- and tetrasubstituted derivatives of anthraquinone, dihydrophenazine, and acridone to investigate cooperativity in a pair of bifurcated hydrogen bonds occurring in the same molecule. The various structures were selected as convenient model systems for three-center hydrocren bonding of both H center dot center dot center dot A center dot center dot center dot H and A center dot center dot center dot H center dot center dot center dot A types. In the former type, the C=O moieties in anthraquinone and acridone act as bifurcated hydrogen bond acceptors, and substituted OH groups act as hydrogen bond donors. In the latter type, the N-H moieties in dihydrophenazine, acridones act as bifurcated hydrogen bond donors, and the carbonyl oxygens of substituted CHO groups act as hydrogen bond acceptors. Different indicators of cooperativity reveal that two intramolecular bifurcated hydrogen bonds simultaneously present in the same molecule significantly reinforce each other.