J Chem Inf Model - Predicting pK(a) values of substituted phenols from atomic charges: comparison of different quantum mechanical methods and charge distribution schemes.


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The acid dissociation (ionization) constant pK(a) is one of the fundamental properties of organic molecules. We have evaluated different computational strategies and models to predict the pK(a) values of substituted phenols using partial atomic charges. Partial atomic charges for 124 phenol molecules were calculated using 83 approaches containing seven theory levels (MP2, HF, B3LYP, BLYP, BP86, AM1, and PM3), three basis sets (6-31G*, 6-311G, STO-3G), and five population analyses (MPA, NPA, Hirshfeld, MK, and Lo?wdin). The correlations between pK(a) and various atomic charge descriptors were examined, and the best descriptors were selected for preparing the quantitative structure-property relationship (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 pK(a)s predicted by most of the models correlate strongly with experimental pK(a) values. For example, more than 25% of the models have correlation coefficients (R?) greater than 0.95 and root-mean-square errors smaller than 0.49. All seven examined theory levels are applicable for pK(a) 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*. The 6-311G basis set provided slightly weaker correlations, and unexpectedly also, the STO-3G basis set is applicable for the QSPR modeling of pK(a). The Mulliken, natural, and Lo?wdin population analyses provide accurate models for all tested theory levels and basis sets. The results provided by the Hirshfeld population analysis were also acceptable, but the QSPR models based on MK charges show only weak correlations.

Resumo Limpo

acid dissoci ioniz constant pka one fundament properti organ molecul evalu differ comput strategi model predict pka valu substitut phenol use partial atom charg partial atom charg phenol molecul calcul use approach contain seven theori level mp hf blyp blyp bp pm three basi set g g stog five popul analys mpa npa hirshfeld mk lowdin correl pka various atom charg descriptor examin best descriptor select prepar quantit structureproperti relationship qspr model one qspr model creat approach charg calcul accuraci model analyz compar pkas predict model correl strong experiment pka valu exampl model correl coeffici r greater rootmeansquar error smaller seven examin theori level applic pka predict charg best result obtain mp hf level theori suitabl basi set found g g basi set provid slight weaker correl unexpect also stog basi set applic qspr model pka mulliken natur lowdin popul analys provid accur model test theori level basi set result provid hirshfeld popul analysi also accept qspr model base mk charg show weak correl

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