A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids

This study presents a detailed thermodynamic investigation on the protonation behavior of tartronic acid in aqueous solutions of various ionic media, including sodium chloride, potassium chloride, tetramethylammonium chloride, and tetraethylammonium iodide. Specifically, potentiometric measurements...

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Main Authors: Gabriele Lando, Clemente Bretti, Paola Cardiano, Anna Irto, Demetrio Milea, Concetta De Stefano
Format: Article
Language:English
Published: MDPI AG 2025-03-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/30/7/1497
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author Gabriele Lando
Clemente Bretti
Paola Cardiano
Anna Irto
Demetrio Milea
Concetta De Stefano
author_facet Gabriele Lando
Clemente Bretti
Paola Cardiano
Anna Irto
Demetrio Milea
Concetta De Stefano
author_sort Gabriele Lando
collection DOAJ
description This study presents a detailed thermodynamic investigation on the protonation behavior of tartronic acid in aqueous solutions of various ionic media, including sodium chloride, potassium chloride, tetramethylammonium chloride, and tetraethylammonium iodide. Specifically, potentiometric measurements were performed at temperatures ranging from 288.15 to 310.15 K and ionic strengths between 0.1 and 1.0 mol dm<sup>−3</sup> to determine stoichiometric protonation constants in different ionic media. The formation of weak complexes between tartronate and alkaline metal cations was obtained by means of the Δ<i>pK</i> method. Moreover, data were modeled using the Debye–Hückel equation and Specific Ion Interaction Theory (SIT), allowing for the calculation of standard thermodynamic parameters and the assessment of the dependence of protonation constants on ionic strength. Additionally, the protonation behavior of tartronic acid was compared with that of structurally related acids, such as malonic and mesoxalic acids, providing insights into the role of molecular structure in acid dissociation. The results emphasize the significant role of entropic contributions in the protonation process and provide a comprehensive model for the thermodynamic properties of tartronic acid across a wide range of experimental conditions.
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spelling doaj-art-2f380ed84751442f934c987a4eaf11f52025-08-20T03:06:35ZengMDPI AGMolecules1420-30492025-03-01307149710.3390/molecules30071497A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural FluidsGabriele Lando0Clemente Bretti1Paola Cardiano2Anna Irto3Demetrio Milea4Concetta De Stefano5Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Viale Ferdinando Stagno d’Alcontres, 31, I-98166 Messina, ItalyThis study presents a detailed thermodynamic investigation on the protonation behavior of tartronic acid in aqueous solutions of various ionic media, including sodium chloride, potassium chloride, tetramethylammonium chloride, and tetraethylammonium iodide. Specifically, potentiometric measurements were performed at temperatures ranging from 288.15 to 310.15 K and ionic strengths between 0.1 and 1.0 mol dm<sup>−3</sup> to determine stoichiometric protonation constants in different ionic media. The formation of weak complexes between tartronate and alkaline metal cations was obtained by means of the Δ<i>pK</i> method. Moreover, data were modeled using the Debye–Hückel equation and Specific Ion Interaction Theory (SIT), allowing for the calculation of standard thermodynamic parameters and the assessment of the dependence of protonation constants on ionic strength. Additionally, the protonation behavior of tartronic acid was compared with that of structurally related acids, such as malonic and mesoxalic acids, providing insights into the role of molecular structure in acid dissociation. The results emphasize the significant role of entropic contributions in the protonation process and provide a comprehensive model for the thermodynamic properties of tartronic acid across a wide range of experimental conditions.https://www.mdpi.com/1420-3049/30/7/1497tartronic acidprotonation constantsionic strengththermodynamic modelingSpecific Ion Interaction Theory (SIT)weak complex formation
spellingShingle Gabriele Lando
Clemente Bretti
Paola Cardiano
Anna Irto
Demetrio Milea
Concetta De Stefano
A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
Molecules
tartronic acid
protonation constants
ionic strength
thermodynamic modeling
Specific Ion Interaction Theory (SIT)
weak complex formation
title A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
title_full A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
title_fullStr A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
title_full_unstemmed A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
title_short A Comprehensive Equilibrium Analysis of Tartronate with Proton and Major Cations in Natural Fluids
title_sort comprehensive equilibrium analysis of tartronate with proton and major cations in natural fluids
topic tartronic acid
protonation constants
ionic strength
thermodynamic modeling
Specific Ion Interaction Theory (SIT)
weak complex formation
url https://www.mdpi.com/1420-3049/30/7/1497
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