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The use of chemical shifts vs. coupling constants for studying tautomerism: a combined experimental and theoretical approach

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Abstract

When observing average NMR signals originated from a rapid equilibrium, the procedure to estimate the composition of the mixture is to use interpolation. To illustrate the difficulties of this approach, the much-studied case of the NH and OH tautomers of pyrazolinones will be reexamined. Calculated absolute shieldings and coupling constants were compared with experimental data. Although the large predominance of the OH tautomer in DMSO was confirmed, the result is a little disappointing because no consistency in the percentages was achieved using chemical shifts and coupling constants.

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Acknowledgments

Thanks are given to MCyT (project number BQU2003-00976) and to MEC (project number CTQ2006-02586) of Spain for financial support.

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Correspondence to Ibon Alkorta.

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Sanz, D., Claramunt, R.M., Alkorta, I. et al. The use of chemical shifts vs. coupling constants for studying tautomerism: a combined experimental and theoretical approach. Struct Chem 18, 703–708 (2007). https://doi.org/10.1007/s11224-007-9208-4

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  • DOI: https://doi.org/10.1007/s11224-007-9208-4

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