Equilibrium Acidities of Superacids

• Published in: Journal of organic chemistry Vol. 76; no. 2; pp. 391 - 395
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 21.01.2011
• Subjects: Chemical reactivity; Chemistry; Exact sciences and technology; Organic chemistry; Reactivity and mechanisms; Characterization; Nitrile; Superacid; Picric acid; Polarity; Acidity; Strong acid; Solvent; Sulfuric acid; Hydrogen bromide
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo101409p

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.