A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids
Abstract
The pK(a) values of twelve beta-hydroxy-beta-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)pK(a) of a compound. Using (s)(w)pKa in previously established equations for the specific methanol/buffer mixture, the (w)(w)pK(a) values (in pure water) were calculated. The obtained wwpKa values for the synthesized compounds were in a range from 3.40 to 3.74, and the (w)(w)pK(a) for ibuprofen was 4.27. The Predicted pK(a) 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 pK(a) values were calculated as a wide range.
Keywords:
dissociation constant / anti-inflammatory compounds / ibuprofen / liquid chromatography / carboxylic acidsSource:
Journal of the Serbian Chemical Society, 2018, 83, 7-8, 875-883Publisher:
- Srpsko hemijsko društvo, Beograd
Funding / projects:
- Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-MESTD-Basic Research (BR or ON)-172041)
DOI: 10.2298/JSC170804045S
ISSN: 0352-5139
WoS: 000441529600007
Scopus: 2-s2.0-85082361980
Collections
Institution/Community
PharmacyTY - JOUR AU - Savić, Jelena AU - Dilber, Sanda AU - Vujić, Zorica AU - Vladimirov, Sote AU - Brborić, Jasmina PY - 2018 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3069 AB - The pK(a) values of twelve beta-hydroxy-beta-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)pK(a) of a compound. Using (s)(w)pKa in previously established equations for the specific methanol/buffer mixture, the (w)(w)pK(a) values (in pure water) were calculated. The obtained wwpKa values for the synthesized compounds were in a range from 3.40 to 3.74, and the (w)(w)pK(a) for ibuprofen was 4.27. The Predicted pK(a) 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 pK(a) values were calculated as a wide range. PB - Srpsko hemijsko društvo, Beograd T2 - Journal of the Serbian Chemical Society T1 - A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids VL - 83 IS - 7-8 SP - 875 EP - 883 DO - 10.2298/JSC170804045S ER -
@article{ author = "Savić, Jelena and Dilber, Sanda and Vujić, Zorica and Vladimirov, Sote and Brborić, Jasmina", year = "2018", abstract = "The pK(a) values of twelve beta-hydroxy-beta-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)pK(a) of a compound. Using (s)(w)pKa in previously established equations for the specific methanol/buffer mixture, the (w)(w)pK(a) values (in pure water) were calculated. The obtained wwpKa values for the synthesized compounds were in a range from 3.40 to 3.74, and the (w)(w)pK(a) for ibuprofen was 4.27. The Predicted pK(a) 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 pK(a) values were calculated as a wide range.", publisher = "Srpsko hemijsko društvo, Beograd", journal = "Journal of the Serbian Chemical Society", title = "A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids", volume = "83", number = "7-8", pages = "875-883", doi = "10.2298/JSC170804045S" }
Savić, J., Dilber, S., Vujić, Z., Vladimirov, S.,& Brborić, J.. (2018). A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids. in Journal of the Serbian Chemical Society Srpsko hemijsko društvo, Beograd., 83(7-8), 875-883. https://doi.org/10.2298/JSC170804045S
Savić J, Dilber S, Vujić Z, Vladimirov S, Brborić J. A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids. in Journal of the Serbian Chemical Society. 2018;83(7-8):875-883. doi:10.2298/JSC170804045S .
Savić, Jelena, Dilber, Sanda, Vujić, Zorica, Vladimirov, Sote, Brborić, Jasmina, "A modified RP-HPLC method for the determination of the pK(a) values of synthesized beta-hydroxy-beta-arylalkanoic acids" in Journal of the Serbian Chemical Society, 83, no. 7-8 (2018):875-883, https://doi.org/10.2298/JSC170804045S . .