A method for the calculation of the intramolecular hydrogen bond (HB) energy (EHB) by molecular tailoring approach for hydroxycarbonyl aliphatic compounds has been used for compounds with resonance-assisted hydrogen bonding (RAHB). The intramolecular hydrogen bond energies estimated for 229 structures (of 186 compounds) range from 8.2 to 26.3 kcal/mol and show correlation with the geometry descriptors of hydrogen bonds, with the calculated frequencies as well as with topological parameters obtained from the atoms in molecules (AIM) theory. These correlations differ significantly from obtained formerly for saturated nonenolizable structures and prove the special character of the resonance-assisted hydrogen-bonded systems.