Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters

Gergő Dargó, Adrienn Bölcskei, A. Grün, S. Béni, Zoltán Szántó, Antal Lopata, G. Keglevich, György T. Balogh

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Determination of the proton dissociation constants of several arylphosphonic acid derivatives was carried out to investigate the accuracy of the Hammett equations available for this family of compounds. For the measurement of the pKa values modern, accurate methods, such as the differential potentiometric titration and NMR-pH titration were used. We found our results significantly different from the pKa values reported before (pKa1: MAE  =  0.16 pKa2: MAE = 0.59). Based on our recently measured pKa values, refined Hammett equations were determined that might be used for predicting highly accurate ionization constants of newly synthesized compounds (pKa1 = 1.70–0.894σ, pKa2 = 6.92–0.934σ).

Original languageEnglish
Pages (from-to)101-109
Number of pages9
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume143
DOIs
Publication statusPublished - Sep 5 2017

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Titration
Protons
Acids
Ionization
Nuclear magnetic resonance
Derivatives

Keywords

  • Arylphosphonic acids
  • Hammett equation
  • NMR-pH titration
  • pH-metric pK measurements
  • pK predictors

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

Cite this

Proton dissociation properties of arylphosphonates : Determination of accurate Hammett equation parameters. / Dargó, Gergő; Bölcskei, Adrienn; Grün, A.; Béni, S.; Szántó, Zoltán; Lopata, Antal; Keglevich, G.; Balogh, György T.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 143, 05.09.2017, p. 101-109.

Research output: Contribution to journalArticle

Dargó, Gergő ; Bölcskei, Adrienn ; Grün, A. ; Béni, S. ; Szántó, Zoltán ; Lopata, Antal ; Keglevich, G. ; Balogh, György T. / Proton dissociation properties of arylphosphonates : Determination of accurate Hammett equation parameters. In: Journal of Pharmaceutical and Biomedical Analysis. 2017 ; Vol. 143. pp. 101-109.
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AU - Szántó, Zoltán

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