A detailed QSPR investigation of the water solubility (logS) of 1063 solid neutral chemicals, agrochemicals, drugs and prodrugs has been carried out. The application of the “General Solubility Equation” of Yalkowsky et al. resulted in a correlation between experimental and calculated solubility with rather modest statistic criteria. It was found that 191 compounds (18%) have calculated logS with deviations above one logarithmic unit. A comparison of experimental values with those calculated by an equation previously derived for liquid chemicals demonstrates that a part of the total set of compounds containing certain substructures such as chloroalkyls, phenyls, biphenyls, nitrogen (acyclic and in cycles), benzanthracenes, phenols, and chemicals with ether, ester, and N,N‐disubstituted carboxamide groups obey to the equation for liquids. Not unexpectedly, the other part of compounds containing both strong H‐bond acceptor and donor groups is essentially less soluble than calculated for compounds in the liquid state. It is proposed that this low solubility is connected with a specific H‐bond association of these compounds in their crystal lattice.
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Raevsky et al. (2004) studied this question.
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