NMR method for the determination of solute hydrogen bond acidity

The Journal of Organic Chemistry
Michael H AbrahamLee Griffiths

Abstract

It is shown that the difference in the 1H NMR chemical shift of a protic hydrogen in DMSO and CDCl3 solvents is directly related to the overall, or summation, hydrogen bond acidity for a wide range of solutes. This provides a new and direct method of measuring the hydrogen bond acidity. For 54 compounds, the observed shifts for 72 protic hydrogens could be correlated to the Abraham solute hydrogen bond acidity parameter, A, with a correlation coefficient squared, R2, of 0.938 and a standard deviation, SD, of 0.054 units in A. A training equation that used half the data could predict A values for the remaining data with an average error of 0.001 and a standard deviation, SD, of 0.053 units, thus demonstrating the predictive power of the method. Unlike any previous method for the determination of solute hydrogen bond acidities, the NMR method allows the determination of A values for individual protic hydrogens in multifunctional solutes.

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Citations

Mar 11, 2010·Proceedings of the National Academy of Sciences of the United States of America·Jeffrey J Warren, James M Mayer
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Sep 9, 2016·The Journal of Organic Chemistry·Yossi ZafraniEytan Gershonov
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Jun 3, 2021·Chemical Society Reviews·Jeroen B I SapVéronique Gouverneur
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Sep 4, 2021·Chemical Science·Guy KleksAnthony R Carroll

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