Publication Details |
Category | Text Publication |
Reference Category | Journals |
DOI | 10.1897/01-605 |
Title (Primary) | Quantitative structure-property relationships for predicting Henry's law constant from molecular structure |
Author | Dearden, J.C.; Schüürmann, G. |
Journal | Environmental Toxicology and Chemistry |
Year | 2003 |
Department | OEC |
Volume | 22 |
Issue | 8 |
Page From | 1755 |
Page To | 1770 |
Language | englisch |
Keywords | Henry's law constant; Air-water partition coefficient; Quantitative structure-property relationship; Prediction |
Abstract | Various models are available for the prediction of Henry's law constant (H) or the air-water partition coefficient (K(aw)), its dimensionless counterpart. Incremental methods are based on structural features such as atom types, bond types, and local structural environments; other regression models employ physicochemical properties, structural descriptors such as connectivity indices. and descriptors reflecting the electronic structure. There are also methods to calculate H from the ratio of vapor pressure (p(v)) and water solubility (S(w)) that in turn can be estimated from molecular structure, and quantum chemical continuum-solvation models to predict H via the solvation-free energy (DeltaG(s)). This review is confined to methods that calculate H from molecular structure without experimental information and covers more than 40 methods published in the last 26 years. For a subset of eight incremental methods and four continuum-solvation models, a comparative analysis of their prediction performance is made using a test set of 700 compounds that includes a significant number of more complex and drug-like chemical structures. The results reveal substantial differences in the application range as well as in the prediction capability, a general decrease in prediction performance with decreasing H, and surprisingly large individual prediction errors, which are particularly striking for some quantum chemical schemes. The overall best-performing method appears to be the bond contribution method as implemented in the HENRYWIN software package, yielding a predictive squared correlation coefficient (q(2)) of 0.87 and a standard error of 1.03 log units for the test set. |
Persistent UFZ Identifier | https://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=4779 |
Dearden, J.C., Schüürmann, G. (2003): Quantitative structure-property relationships for predicting Henry's law constant from molecular structure Environ. Toxicol. Chem. 22 (8), 1755 - 1770 |