Tautomerism of pyridinylbutane-1,3-diones : An NMR and DFT study
© 2023 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.
| Publié dans: | Magnetic resonance in chemistry : MRC. - 1985. - 61(2023), 6 vom: 22. Juni, Seite 356-362 |
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| Auteur principal: | |
| Autres auteurs: | , , |
| Format: | Article en ligne |
| Langue: | English |
| Publié: |
2023
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| Accès à la collection: | Magnetic resonance in chemistry : MRC |
| Sujets: | Journal Article DFT calculations NMR hydrogen bonding isotope effects on chemical shifts pyridinylbutane-1,3-diones tautomerism β-diketones |
| Résumé: | © 2023 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd. The three possible 1-(n-pyridinyl)butane-1,3-diones (nPM) have been synthesized. Structures, tautomerism, and conformations are investigated by means of DFT calculations. 1 H and 13 C NMR spectra are assigned, and deuterium isotope effects on 13 C chemical shifts have been measured. Analysis of the isotope effects leads to the equilibrium constants of the keto-enol tautomers. Some interesting differences are seen between the three compounds and the phenyl analogs. The isotope effects can also rank the hydrogen bonds of the compounds, with the one with nitrogen in the three positions of the pyridine ring as the weakest. Structures, conformers, energies, and NMR nuclear shieldings are calculated using DFT calculations at the B3LYP/6-311++G(d,p) level |
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| Description: | Date Completed 10.05.2023 Date Revised 10.05.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
| ISSN: | 1097-458X |
| DOI: | 10.1002/mrc.5342 |