Details zur Publikation |
| Kategorie | Textpublikation |
| Referenztyp | Zeitschriften |
| DOI | 10.1021/ci900040z |
| Titel (primär) | Prediction of the intrinsic hydrogen bond acceptor strength of organic compounds by local molecular parameters |
| Autor | Schwöbel, J.; Ebert, R.-U.; Kühne, R.
; Schüürmann, G. |
| Quelle | Journal of Chemical Information and Modeling |
| Erscheinungsjahr | 2009 |
| Department | OEC |
| Band/Volume | 49 |
| Heft | 4 |
| Seite von | 956 |
| Seite bis | 962 |
| Sprache | englisch |
| Abstract | A quantum chemical model has been developed for predicting the hydrogen bond (HB) acceptor strength of monofunctional organic compounds from electronic ground-state properties of the single molecules. Local molecular parameters are used to quantify electrostatic, polarizability, and charge transfer components to hydrogen bonding, employing the ab initio and density functional theory levels HF/6-31G** and B3LYP/6-31G**. The model can handle lone pairs of intermediate and strong 1113 acceptor heteroatoms (N, O, S) as well as of weak HB acceptor halogens (F, Cl, Br) and includes also olefinic, alkyne, and aromatic pi-bonds as weak HB acceptor sites. The model calibration with 403 compounds and experimental values for the Abraham HB acceptor strength B yielded squared correlation coefficients r(2) around 0.95, outperforming existing fragment-based schemes. Model validation was performed applying a leave-50%-out procedure, yielding predictive squared correlation coefficients q(2) of around 0.95 for the subsets that both cover the whole chemical domain as well as (almost) the whole target value range of the data set |
| dauerhafte UFZ-Verlinkung | https://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=604 |
| Schwöbel, J., Ebert, R.-U., Kühne, R., Schüürmann, G. (2009): Prediction of the intrinsic hydrogen bond acceptor strength of organic compounds by local molecular parameters J. Chem Inf. Model. 49 (4), 956 - 962 10.1021/ci900040z |
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