Dissociation constants of perfluoroalkanoic acids

Dissociation constants of perfluoroalkanoic acids Monatsh Chem (2017) 148:1679–1684 DOI 10.1007/s00706-017-1970-4 ORIGINAL PAPER Dissociation constants of perfluoroalkanoic acids 1,2 1 1 • • Radom´ırCabala Karel Nesmeˇra´k Tereza Vlasa´kova´ Received: 27 February 2017 / Accepted: 19 March 2017 / Published online: 4 July 2017 Springer-Verlag Wien 2017 Abstract The dissociation constants of six selected per- Introduction fluoroalkanoic acids (from perfluoropentanoic to perfluorodecanoic acid) were determined using neutraliza- Perfluorinated carboxylic acids (PFCAs) are purely tion potentiometric titration method. The values of anthropogenic compounds, except trifluoroacetic acid, determined dissociation constants ranges from pK = 2.17 which is thought to have significant natural sources [1]. to 2.44, and they are in partial agreement with published PFCAs are substitution derivatives of carboxylic acids data which have also been reviewed. The decrease of value where all the hydrogen atoms in the alkyl chain are of dissociation constant with increasing number of carbon replaced by fluorine atoms. The very strong chemical C–F in alkyl chain has been observed. Also, the increase of bond (dissociation energy of approx. 460 kJ/mol) causes values of dissociation constants of perfluoroalkanoic acids strong difference in physicochemical properties of PFCAs in comparison with their nonfluorinated analogs has been compared to their nonfluorinated analogs. High ionization confirmed. energy http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

Dissociation constants of perfluoroalkanoic acids

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Publisher
Springer Vienna
Copyright
Copyright © 2017 by Springer-Verlag Wien
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-017-1970-4
Publisher site
See Article on Publisher Site

Abstract

Monatsh Chem (2017) 148:1679–1684 DOI 10.1007/s00706-017-1970-4 ORIGINAL PAPER Dissociation constants of perfluoroalkanoic acids 1,2 1 1 • • Radom´ırCabala Karel Nesmeˇra´k Tereza Vlasa´kova´ Received: 27 February 2017 / Accepted: 19 March 2017 / Published online: 4 July 2017 Springer-Verlag Wien 2017 Abstract The dissociation constants of six selected per- Introduction fluoroalkanoic acids (from perfluoropentanoic to perfluorodecanoic acid) were determined using neutraliza- Perfluorinated carboxylic acids (PFCAs) are purely tion potentiometric titration method. The values of anthropogenic compounds, except trifluoroacetic acid, determined dissociation constants ranges from pK = 2.17 which is thought to have significant natural sources [1]. to 2.44, and they are in partial agreement with published PFCAs are substitution derivatives of carboxylic acids data which have also been reviewed. The decrease of value where all the hydrogen atoms in the alkyl chain are of dissociation constant with increasing number of carbon replaced by fluorine atoms. The very strong chemical C–F in alkyl chain has been observed. Also, the increase of bond (dissociation energy of approx. 460 kJ/mol) causes values of dissociation constants of perfluoroalkanoic acids strong difference in physicochemical properties of PFCAs in comparison with their nonfluorinated analogs has been compared to their nonfluorinated analogs. High ionization confirmed. energy

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Jul 4, 2017

References

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