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Solute descriptors characterizing major interactions in solution are accessible based on quantitative structure-property relationships (QSPR). Parameters of such relationships should be additive for functional groups. Because added parameters of monools describing molecular interaction do not meet the experimentally found intermolecular interaction parameters of diols and triols, it is assumed that intramolecular hydrogen bonding is responsible for these deviations. In this paper the intramolecular interactions in several diols are illuminated by IR measurements. Particularly, the influence of intramolecular hydrogen bonding on the absorbances of the OH groups is subject of investigation. Two conclusions can be drawn from the results: The terminal OH groups, which underlie an OH–OH interaction, also change their absorbance intensity in comparison to the free OH band. Secondly, the intermolecular interaction potential is strongly affected by intramolecular hydrogen bonding. The first observation is tentatively quantified as well as the position of the equilibrium between intramolecularly bonded and free diols.