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Issue 10, 2017
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A unified view to Brønsted acidity scales: do we need solvated protons?

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Abstract

The most comprehensive solvent acidity scale spanning 28 orders of magnitude of acidity was measured in the low-polarity solvent 1,2-dichloroethane (DCE). Its experimental core is linked to the unified acidity scale (pHabs) in an unprecedented and generalized approach only based on experimental values. This enables future measurements of acid strengths and acidity adjustments in low polarity solvents. The scale was cross-validated computationally. The purely experimental and computational data agree very well. The DCE scale includes 87 buffer systems with Image ID:c7sc01424d-t1.gif values between −13.0 and +15.4, i.e. similar to water at hypothetical and extreme pH values of −13.0 to +15.4. Unusually, such high acidities in DCE are not realized via solvated protons, but rather through strongly acidic molecules able to directly donate their proton, even to weak bases dissolved in the solution. Thus, in all examined cases, not a single solvated proton is present in one liter of DCE.

Graphical abstract: A unified view to Brønsted acidity scales: do we need solvated protons?

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Publication details

The article was received on 30 Mar 2017, accepted on 03 Aug 2017 and first published on 07 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC01424D
Citation: Chem. Sci., 2017,8, 6964-6973
  • Open access: Creative Commons BY license
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    A unified view to Brønsted acidity scales: do we need solvated protons?

    E. Paenurk, K. Kaupmees, D. Himmel, A. Kütt, I. Kaljurand, I. A. Koppel, I. Krossing and I. Leito, Chem. Sci., 2017, 8, 6964
    DOI: 10.1039/C7SC01424D

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