A modified RP-HPLC method for determination of pKa values of synthesized β-hydroxy-β-arylalkanoic acids

Jelena S. Savić, Sanda P. Dilber, Zorica B. Vujić, Sote M. Vladimirov, Jasmina S. Brborić

Abstract


pKa values of twelve β-hydroxy-β-arylalkanoic acids and ibuprofen were determined using modified RP-HPLC method. Stationary phase was octadecyl modified (C-18) silica gel, and mobile phases were mixtures of methanol and one of ten different buffers (60:40, v/v). Mean retention time of each compound was plotted against pH of each of ten used mobile phases. Inflection point of obtained sigmoidal curve represents  of a compound. Usingin previously established equations for the specific methanol/buffer mixture, values (in pure water) were calculated. Obtained values for synthesized compounds were in a range from 3.40 to 3.75, and for ibuprofen was 4.27. Predicted pKa values for this type of compounds in MarvinSketch 5.11.5. program were in a poor correlation with experimental results, while in ACD/I-Labs pKa values were calculated as a wide range.


Keywords


dissociation constant; anti-inflammatory compounds; ibuprofen; liquid chromatography; carboxylic acids

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