A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids
The pKa values of twelve β-hydroxy-β-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 retent...
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Serbian Chemical Society
2018-01-01
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doaj-4c901a75bd8e483d933a923066a3a9012020-11-24T21:33:23ZengSerbian Chemical Society Journal of the Serbian Chemical Society0352-51391820-74212018-01-01837-887588310.2298/JSC170804045S0352-51391800045SA modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acidsSavić Jelena S.0Dilber Sanda P.1Vujić Zorica B.2Vladimirov Sote M.3Brborić Jasmina S.4Faculty of Pharmacy, BelgradeFaculty of Pharmacy, BelgradeFaculty of Pharmacy, BelgradeFaculty of Pharmacy, BelgradeFaculty of Pharmacy, BelgradeThe pKa values of twelve β-hydroxy-β-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. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172041]http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391800045S.pdfdissociation constantanti-inflammatory compoundsibuprofenliquid chromatographycarboxylic acids |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Savić Jelena S. Dilber Sanda P. Vujić Zorica B. Vladimirov Sote M. Brborić Jasmina S. |
spellingShingle |
Savić Jelena S. Dilber Sanda P. Vujić Zorica B. Vladimirov Sote M. Brborić Jasmina S. A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids Journal of the Serbian Chemical Society dissociation constant anti-inflammatory compounds ibuprofen liquid chromatography carboxylic acids |
author_facet |
Savić Jelena S. Dilber Sanda P. Vujić Zorica B. Vladimirov Sote M. Brborić Jasmina S. |
author_sort |
Savić Jelena S. |
title |
A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids |
title_short |
A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids |
title_full |
A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids |
title_fullStr |
A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids |
title_full_unstemmed |
A modified RP-HPLC method for the determination of the pKa values of synthesized β-hydroxy-β-arylalkanoic acids |
title_sort |
modified rp-hplc method for the determination of the pka values of synthesized β-hydroxy-β-arylalkanoic acids |
publisher |
Serbian Chemical Society |
series |
Journal of the Serbian Chemical Society |
issn |
0352-5139 1820-7421 |
publishDate |
2018-01-01 |
description |
The pKa values of twelve β-hydroxy-β-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. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172041] |
topic |
dissociation constant anti-inflammatory compounds ibuprofen liquid chromatography carboxylic acids |
url |
http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391800045S.pdf |
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