| SVOBODOVÁ VAŘEKOVÁ, Radka, Stanislav GEIDL, Crina-Maria IONESCU, Ondřej SKŘEHOTA, Michal KUDERA, David SEHNAL, Tomáš BOUCHAL, Ruben A. ABAGYAN, Heinrich J. HUBER a Jaroslav KOČA. Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes. Journal of Chemical Information and Modeling. 2011, roč. 51, č. 8, s. 1795-1806. ISSN 1549-9596. |
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@article{950090,
author = {Svobodová Vařeková, Radka and Geidl, Stanislav and Ionescu, CrinaandMaria and Skřehota, Ondřej and Kudera, Michal and Sehnal, David and Bouchal, Tomáš and Abagyan, Ruben A. and Huber, Heinrich J. and Koča, Jaroslav},
article_number = {8},
keywords = {pka; pka prediction; charge; QSPR; population analysis; quantum meechanics},
language = {eng},
issn = {1549-9596},
journal = {Journal of Chemical Information and Modeling},
title = {Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes},
volume = {51},
year = {2011}
}
TY - JOUR
ID - 950090
AU - Svobodová Vařeková, Radka - Geidl, Stanislav - Ionescu, Crina-Maria - Skřehota, Ondřej - Kudera, Michal - Sehnal, David - Bouchal, Tomáš - Abagyan, Ruben A. - Huber, Heinrich J. - Koča, Jaroslav
PY - 2011
TI - Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes
JF - Journal of Chemical Information and Modeling
VL - 51
IS - 8
SP - 1795-1806
EP - 1795-1806
SN - 15499596
KW - pka
KW - pka prediction
KW - charge
KW - QSPR
KW - population analysis
KW - quantum meechanics
N2 - The acid dissociation (ionisation) constant pKa is one of the fundamental properties of organic molecules. We have evaluated different computational strategies and models to predict the pKa values of substituted phenols using partial atomic charges. Partial atomic charges for 124 phenol molecules were calculated using 83 approaches containing seven theory levels, three basis sets and five population analyses. The correlations between pKa and various atomic charge descriptors were examined and the best descriptors were selected for preparing the QSPR models. One QSPR model was created for each of the 83 approaches to charge calculation, and then the accuracy of all these models was analyzed and compared. The pKas predicted by most of the models correlate strongly with experimental pKa values. All seven examined theory levels are applicable for pKa prediction from charges. The best results were obtained for the MP2 and HF level of theory. The most suitable basis set was found to be 6-31G*.
ER -
SVOBODOVÁ VAŘEKOVÁ, Radka, Stanislav GEIDL, Crina-Maria IONESCU, Ondřej SKŘEHOTA, Michal KUDERA, David SEHNAL, Tomáš BOUCHAL, Ruben A. ABAGYAN, Heinrich J. HUBER a Jaroslav KOČA. Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes. \textit{Journal of Chemical Information and Modeling}. 2011, roč.~51, č.~8, s.~1795-1806. ISSN~1549-9596.
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