Water Solubilities of Polynuclear Aromatic and Heteroaromatic Compounds

The water solubilities of several polynuclear aromatic and heteroaromatic hydrocarbons have been compiled and reviewed for consistency through correlations with parameters such as surface area, molecular volume, and boiling point. The carbocycles and oxygen and sulfur heterocycles were governed by the same correlative equations, thereby indicating that these heteroatoms entered into only a limited degree of hydrogen bonding. Equations representing the nitrogen heterocycles differed from their carbocyclic counterparts by an approximately constant amount, suggesting that while the solubilizing effect of the nitrogen heteroatom may be large, it tends to remain constant within a similar series of compounds.