Estimating the pKa of phenols, carboxylic acids and alcohols from semi-empirical quantum chemical methods

Quantitative structure property relationships (QSPR) for the pKa of phenols, carboxylic acids and alcohols were developed from descriptors derived from semi-empirical molecular orbital theory quantum chemical calculations. A training set of compounds were used to refine the models and a validation s...

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Bibliographic Details
Published inChemosphere (Oxford) Vol. 38; no. 1; pp. 191 - 206
Main Author CITRA, M. J
Format Journal Article
LanguageEnglish
Published Oxford Elsevier 1999
Subjects
Chemistry
Exact sciences and technology
General and physical chemistry
Solution properties
Solutions
Acidity constant
Phenol
Quantum chemistry
Carboxylic acid
Theoretical study
Alcohol
Dissociation constant
Property structure relationship
Semiempirical method
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Summary:Quantitative structure property relationships (QSPR) for the pKa of phenols, carboxylic acids and alcohols were developed from descriptors derived from semi-empirical molecular orbital theory quantum chemical calculations. A training set of compounds were used to refine the models and a validation set of appropriate chemicals were chosen to test the models. Correlation coefficients for the estimated versus observed pKa values were 0.96 for phenols, 0.84 for non-aromatic carboxylic acids, 0.89 for benzoic acids and 0.89 for alcohols. The results obtained by the quantum chemical method are compared to results obtained from linear free energy relationships (LFER) and the merits of each approach are discussed.
Bibliography:ObjectType-Article-1
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ISSN:0045-6535
1879-1298
DOI:10.1016/s0045-6535(98)00172-6