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A joint theoretical and experimental investigation on the 13C and 1H NMR chemical shifts of coumarin derivatives

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Abstract

1H and 13C NMR chemical shifts of coumarin derivatives have been determined using first principles approaches with and without accounting for the effects of the solvent and compared to experiment in order to assess their reliability. Good linear relationships are obtained between theory and experiment, which allows correcting the calculated values for systematic errors. This is particularly the case when using the PCM scheme to model the solvent effects because the δ values larger than 150 ppm are more difficult to reproduce. The final accuracy of the method amounts to about 1 ppm for 13C and 0.05 ppm for 1H.

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Acknowledgments

This work is dedicated to Prof. S. Suhai, a leading scientist in the field of polymer electronic structure calculations. This work was supported from research grants from the Belgian Government (IUAP No P06-27 “Functional Supramolecular Systems”). Ph. d’A. is grateful to the Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture (FRIA) for his PhD grant. E.B. thanks the IUAP program No P06-27 for her postdoctoral grants. B.C. thanks the Belgian National Fund for Scientific Research for his Research Director position and L.M. for her research fellow position. The calculations were performed on the Interuniversity Scientific Computing Facility (ISCF), installed at the Facultés Universitaires Notre-Dame de la Paix (Namur, Belgium), for which the authors gratefully acknowledge the financial support of the FNRS-FRFC, and the “Loterie Nationale” for the convention no 2.4.617.07.F, and of the FUNDP.

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  1. Philippe d’Antuono

    Present address: Institut des Sciences Moléculaires, UMR 5255 CNRS, Université de Bordeaux, Cours de la Libération, 351, 33405, Talence Cedex, France

Authors and Affiliations

  1. Laboratoire de Chimie Théorique Appliquée, Facultés Universitaires Notre-Dame de la Paix (FUNDP), rue de Bruxelles, 61, 5000, Namur, Belgium

    Philippe d’Antuono, Edith Botek & Benoît Champagne

  2. Unité de Chimie des Matériaux Organiques et Inorganiques, Université Catholique de Louvain, Place Louis Pasteur, 1, 1348, Louvain-la-Neuve, Belgium

    Laetitia Maton, Dorothée Taziaux & Jean-Louis Habib-Jiwan

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  1. Philippe d’Antuono
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  2. Edith Botek
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  3. Benoît Champagne
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  6. Jean-Louis Habib-Jiwan
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Correspondence to Benoît Champagne.

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Dedicated to Professor Sandor Suhai on the occasion of his 65th birthday and published as part of the Suhai Festschrift Issue.

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d’Antuono, P., Botek, E., Champagne, B. et al. A joint theoretical and experimental investigation on the 13C and 1H NMR chemical shifts of coumarin derivatives. Theor Chem Acc 125, 461–470 (2010). https://doi.org/10.1007/s00214-009-0625-x

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