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

J 2011

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 et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

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

Abstract

V originále

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

Detailed Information on Publication Record