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

• Published in: Journal of the Serbian Chemical Society Vol. 83; no. 7-8; pp. 875 - 883
• Main Authors: Savic, Jelena, Dilber, Sanda, Vujic, Zorica, Vladimirov, Sote, Brboric, Jasmina
• Format: Journal Article
• Language: English
• Published: Serbian Chemical Society 2018
• Subjects: anti-inflammatory compounds; carboxylic acids; dissociation constant; ibuprofen; liquid chromatography
• ISSN: 0352-5139; 1820-7421
• DOI: 10.2298/JSC170804045S

The pKa values of twelve ?-hydroxy-?-arylalkanoic acids and ibuprofen were determined using a modified RP-HPLC method. The stationary phase was octadecyl modified (C-18) silica gel, and the mobile phases were mixtures of methanol and one of ten different buffers (60:40 volume ratio). The mean retention time of each compound was plotted against the pH of each of the ten used mobile phases. The inflection point of the obtained sigmoidal curve represents the s w pKa of a compound. Using s w pKa in previously established equations for the specific methanol/buffer mixture, the w w pKa values (in pure water) were calculated. The obtained w w pKa values for the synthesized compounds were in a range from 3.40 to 3.74, and the w w pKa for ibuprofen was 4.27. The Predicted pKa values for this type of compounds in the MarvinSketch 5.11.5. Program were in poor correlation with the experimental results, while in ACD/ /I-Labs pKa values were calculated as a wide range.