Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes

SVOBODOVÁ VAŘEKOVÁ, Radka, Stanislav GEIDL, Crina-Maria IONESCU, Ondřej SKŘEHOTA, Michal KUDERA, David SEHNAL, Tomáš BOUCHAL, Ruben A. ABAGYAN, Heinrich J. HUBER and 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. vol. 51, No 8, p. 1795-1806. ISSN 1549-9596. 2011.

Basic information

• Original name: Predicting pK(a) values of substituted phenols from atomic charges: Comparison of different quantum mechanical methods and charge distribution schemes
• Authors: SVOBODOVÁ VAŘEKOVÁ, Radka (203 Czech Republic, guarantor, belonging to the institution), Stanislav GEIDL (203 Czech Republic, belonging to the institution), Crina-Maria IONESCU (642 Romania, belonging to the institution), Ondřej SKŘEHOTA (203 Czech Republic, belonging to the institution), Michal KUDERA (203 Czech Republic, belonging to the institution), David SEHNAL (203 Czech Republic, belonging to the institution), Tomáš BOUCHAL (203 Czech Republic, belonging to the institution), Ruben A. ABAGYAN (840 United States of America), Heinrich J. HUBER (40 Austria) and Jaroslav KOČA (203 Czech Republic, belonging to the institution).
• Edition: Journal of Chemical Information and Modeling, 2011, 1549-9596.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10403 Physical chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 4.675
• RIV identification code: RIV/00216224:14310/11:00049975
• Organization unit: Faculty of Science
• UT WoS: 000294081800007
• Keywords in English: pka; pka prediction; charge; QSPR; population analysis; quantum meechanics
• Tags: AKR, best3, rivok
• Tags: International impact, Reviewed

Abstract

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*.

Links

• GD301/09/H004, research and development project: Name: Molekulární a strukturní biologie vybraných cytostatik. Od mechanistických studií k chemoterapii rakoviny

Investor: Czech Science Foundation

• LC06030, research and development project: Name: Biomolekulární centrum

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre

• ME08008, research and development project: Name: Návrh antibakteriálních a antivirových léků na bázi cukrů a glykomimetik

Investor: Ministry of Education, Youth and Sports of the CR, Design of Carbohydrates and Glycomimetics as Antibacterial and Antiviral Drugs, Research and Development Programme KONTAKT (ME)

• MSM0021622413, plan (intention): Name: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment