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 . 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
Monatshefte für Chemie - Chemical Monthly – Springer Journals
Published: Jul 4, 2017
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