Tautomerism of pyridinylbutane-1,3-diones: An NMR and DFT study

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Standard

Tautomerism of pyridinylbutane-1,3-diones : An NMR and DFT study. / Hansen, Poul Erik; Darugar, Vahidreza; Vakili, Mohammad; Kamounah, Fadhil S.

I: Magnetic Resonance in Chemistry, Bind 61, Nr. 6, 2023, s. 356–362.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Hansen, PE, Darugar, V, Vakili, M & Kamounah, FS 2023, 'Tautomerism of pyridinylbutane-1,3-diones: An NMR and DFT study', Magnetic Resonance in Chemistry, bind 61, nr. 6, s. 356–362. https://doi.org/10.1002/mrc.5342

APA

Hansen, P. E., Darugar, V., Vakili, M., & Kamounah, F. S. (2023). Tautomerism of pyridinylbutane-1,3-diones: An NMR and DFT study. Magnetic Resonance in Chemistry, 61(6), 356–362. https://doi.org/10.1002/mrc.5342

Vancouver

Hansen PE, Darugar V, Vakili M, Kamounah FS. Tautomerism of pyridinylbutane-1,3-diones: An NMR and DFT study. Magnetic Resonance in Chemistry. 2023;61(6):356–362. https://doi.org/10.1002/mrc.5342

Author

Hansen, Poul Erik ; Darugar, Vahidreza ; Vakili, Mohammad ; Kamounah, Fadhil S. / Tautomerism of pyridinylbutane-1,3-diones : An NMR and DFT study. I: Magnetic Resonance in Chemistry. 2023 ; Bind 61, Nr. 6. s. 356–362.

Bibtex

@article{7816df309b0d4beda1d7a6231d30f782,
title = "Tautomerism of pyridinylbutane-1,3-diones: An NMR and DFT study",
abstract = "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. 1H and 13C NMR spectra are assigned, and deuterium isotope effects on 13C 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.",
keywords = "DFT calculations, hydrogen bonding, isotope effects on chemical shifts, NMR, pyridinylbutane-1,3-diones, tautomerism, β-diketones",
author = "Hansen, {Poul Erik} and Vahidreza Darugar and Mohammad Vakili and Kamounah, {Fadhil S.}",
note = "Funding Information: This work was supported by Ferdowsi University of Mashhad, Iran, for providing postdoctoral time for Vahidreza Darugar at Ferdowsi University of Mashhad, Iran. Publisher Copyright: {\textcopyright} 2023 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.",
year = "2023",
doi = "10.1002/mrc.5342",
language = "English",
volume = "61",
pages = "356–362",
journal = "Magnetic Resonance in Chemistry",
issn = "0030-4921",
publisher = "Wiley",
number = "6",

}

RIS

TY - JOUR

T1 - Tautomerism of pyridinylbutane-1,3-diones

T2 - An NMR and DFT study

AU - Hansen, Poul Erik

AU - Darugar, Vahidreza

AU - Vakili, Mohammad

AU - Kamounah, Fadhil S.

N1 - Funding Information: This work was supported by Ferdowsi University of Mashhad, Iran, for providing postdoctoral time for Vahidreza Darugar at Ferdowsi University of Mashhad, Iran. Publisher Copyright: © 2023 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.

PY - 2023

Y1 - 2023

N2 - 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. 1H and 13C NMR spectra are assigned, and deuterium isotope effects on 13C 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.

AB - 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. 1H and 13C NMR spectra are assigned, and deuterium isotope effects on 13C 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.

KW - DFT calculations

KW - hydrogen bonding

KW - isotope effects on chemical shifts

KW - NMR

KW - pyridinylbutane-1,3-diones

KW - tautomerism

KW - β-diketones

U2 - 10.1002/mrc.5342

DO - 10.1002/mrc.5342

M3 - Journal article

C2 - 36882383

AN - SCOPUS:85150898338

VL - 61

SP - 356

EP - 362

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

SN - 0030-4921

IS - 6

ER -

ID: 342495805