Determination of the pKa for caffeic acid in mixed solvent using the net analyte signal method and the ab initio theory

Abbas Dadras; Ali Benvidi; Mansour Namazian; Saleheh Abbasi; Marzieh Dehghan Tezerjani; Moharram Roozgari; Reza Tabaraki

doi:10.2298/JSC180614116D

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Published: Apr 28, 2019

DOI: https://doi.org/10.2298/JSC180614116D

Keywords:

net analyte signal (NAS) caffeic acid acidity constants Gibbs energy change ab initio spectrophotometry

Abbas Dadras

Department of Chemistry, Yazd University, Yazd

Ali Benvidi

Department of Chemistry, Yazd University, Yazd

Mansour Namazian

Department of Chemistry, Yazd University, Yazd

Saleheh Abbasi

Department of Chemistry, Yazd University, Yazd

Marzieh Dehghan Tezerjani

Department of Chemistry, Yazd University, Yazd

Moharram Roozgari

Department of Chemistry, Yazd University, Yazd

Reza Tabaraki

Department of Chemistry, Ilam University, Ilam

Abstract

Due to the biological effects of phenolic acid components, polyphenol-
-rich foods are a significant part of human and animal diets. In this study, the acidity constants of caffeic acid (3,4-dihydroxycinnamic acid) in binary mixtures of ethanol–water were determined spectrophotometrically using the introduced net analyte signal (NAS) algorithm and an ab initio quantum mechanical method. The NAS is an efficient chemometric algorithm for analysis of acid–base equilibrium systems by a spectrophotometric method. At different pH values, the distribution of acid species is obtained from an absorption data matrix and this procedure enabled the pKa of caffeic acid to be obtained alternatively. The results showed that pKa1 (4.02, 4.26, 4.39, 4.57 and 5.11) and pKa2 (8.43, 8.68, 8.79, 9.00 and 9.34) were increased by increasing the percent ethanol in water (0, 10, 20, 30 and 40 vol. %) and these results were in agreement with the results of the Gaussian method. The ab initio calculated Gibbs energy change showed that para-hydroxy group is more acidic than meta-hydroxy group. The red shifts of different species of caffeic acid obtained using the ab initio quantum mechanical method are in good agreement with the results of UV–Vis spectroscopy.

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[1]

A. Dadras, “Determination of the pKa for caffeic acid in mixed solvent using the net analyte signal method and the ab initio theory”, J. Serb. Chem. Soc., vol. 84, no. 4, pp. 391–403, Apr. 2019.

Issue

Vol. 84 No. 4 (2019)

Section

Theoretical Chemistry

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

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