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Published on: August 19, 2013
Acidity Scale in 1,2-Difluorobenzene
John Paulo Samin1, Helerin Roomet1, Märt Lõkov1
1Institute of Chemistry, University of Tartu, Ravila 14a, Tartu 50411, Estonia.
None:
Equilibrium Brønsted acidity measurements have been established in 1,2-difluorobenzene (1,2-DFB), both in terms of acid pK a values measured using UV-vis spectrophotometry and unified pH (pHabs) values measured using differential potentiometry. The pK a values of 137 acids were obtained in 1,2-DFB, of which 33 have been directly measured, spanning 15 orders of magnitude of acidity. The rest have been estimated using pK a values in other solvents (acetonitrile, 1,2-dichloroethane). The pK a values have been anchored to the computational pK a values of 9 compounds. An experimental pHabs scale spanning more than 10 orders of magnitude has been established and aligned with the aqueous pH scale, resulting in a range from -0.6 to 10.0. The potentiometrically measured values and values calculated independently from the experimental pK a values anchored to computational reference values agree well, which demonstrates the solid foundation of the underlying theory. These results open the possibility of quantitatively describing and measuring acid-base processes in 1,2-DFB, including potentiometric and UV-vis spectrophotometric measurement.
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