Structure and spectral characteristics of eight compounds with hydrogen bonds of different strength were calculated at the B3LYP/cc-pVTZ level of theory. A wide range of variation of the hydrogen bond strength in the analyzed compounds allowed us to obtain correlation dependences between the structural characteristics of the hydrogen bridge, the calculated values of the frequencies of stretching vibrations of donor hydroxyl groups, the values of the force constants of hydroxyl and hydrogen bonds, and the dissociation energies of hydrogen bonds. The obtained correlations can be used to evaluate a number of characteristics in compounds with hydrogen bonds.