Equilibrium Acidities of Superacids

In this paper, we report the most comprehensive equilibrium superacidity scale that is available to date. Contrary to most of the past works, this scale is set up in a medium of constant composition and the obtained acidity values characterize the acidities of molecules rather than acidities of medi...

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Veröffentlicht in:Journal of organic chemistry 2011-01, Vol.76 (2), p.391-395
Hauptverfasser: Kütt, Agnes, Rodima, Toomas, Saame, Jaan, Raamat, Elin, Mäemets, Vahur, Kaljurand, Ivari, Koppel, Ilmar A, Garlyauskayte, Romute Yu, Yagupolskii, Yurii L, Yagupolskii, Lev M, Bernhardt, Eduard, Willner, Helge, Leito, Ivo
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container_end_page 395
container_issue 2
container_start_page 391
container_title Journal of organic chemistry
container_volume 76
creator Kütt, Agnes
Rodima, Toomas
Saame, Jaan
Raamat, Elin
Mäemets, Vahur
Kaljurand, Ivari
Koppel, Ilmar A
Garlyauskayte, Romute Yu
Yagupolskii, Yurii L
Yagupolskii, Lev M
Bernhardt, Eduard
Willner, Helge
Leito, Ivo
description In this paper, we report the most comprehensive equilibrium superacidity scale that is available to date. Contrary to most of the past works, this scale is set up in a medium of constant composition and the obtained acidity values characterize the acidities of molecules rather than acidities of media. The current scale is thus complementary to the well-known H 0 scale in the information that it provides. The solvent used is 1,2-dichloroethane (DCE). DCE has very weak basic properties (but sufficiently high polarity) and is an appropriate solvent for measuring acidities of very strong acids of diverse chemical nature. DCE acidities of well-known superacids (CF3SO2OH, (CF3SO2)2NH, cyanocarbon acids, etc.) as well as common mineral acids (H2SO4, HI, HBr, etc.) are reported. Acidities of altogether 62 acids have been determined from 176 interlinked relative acidity measurements. The scale spans 15 orders of magnitude (from picric acid to 1,1,2,3,3-pentacyanopropene) and is expected to be a useful tool in design, use, and further acidity measurements of superacidic molecules.
doi_str_mv 10.1021/jo101409p
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subjects Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
title Equilibrium Acidities of Superacids
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