Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study

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Standard

Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study. / Vakili, Mohammad; Darugar, Vahidreza; Kamounah, Fadhil S.; Erik Hansen, Poul; Hermann, Mathias; Pittelkow, Michael.

In: Journal of Molecular Liquids, Vol. 383, 122074, 2023.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Vakili, M, Darugar, V, Kamounah, FS, Erik Hansen, P, Hermann, M & Pittelkow, M 2023, 'Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study', Journal of Molecular Liquids, vol. 383, 122074. https://doi.org/10.1016/j.molliq.2023.122074

APA

Vakili, M., Darugar, V., Kamounah, F. S., Erik Hansen, P., Hermann, M., & Pittelkow, M. (2023). Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study. Journal of Molecular Liquids, 383, [122074]. https://doi.org/10.1016/j.molliq.2023.122074

Vancouver

Vakili M, Darugar V, Kamounah FS, Erik Hansen P, Hermann M, Pittelkow M. Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study. Journal of Molecular Liquids. 2023;383. 122074. https://doi.org/10.1016/j.molliq.2023.122074

Author

Vakili, Mohammad ; Darugar, Vahidreza ; Kamounah, Fadhil S. ; Erik Hansen, Poul ; Hermann, Mathias ; Pittelkow, Michael. / Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study. In: Journal of Molecular Liquids. 2023 ; Vol. 383.

Bibtex

@article{3c55a75595b54dae98a808a904e8e36b,
title = "Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study",
abstract = "Three 1-(n-pyridinyl)butane-1,3-diones (nPM) (n = 2, 3, and 4) molecules were synthesized and their molecular structure, tautomerism, conformational stability, and intramolecular hydrogen bonding (IHB) of cis-enol forms, was investigated by a combination of computational and experimental methods. Density functional theory (DFT) calculations were used and the Atoms in Molecules (AIM) analysis indicated an intramolecular hydrogen bond strength as 17.9–20.3 kcal/mol using the B3LYP/6–311++G(d,p) level of theory. The calculated structures, NBO, and intramolecular hydrogen bond strengths for the stable cis-enol forms of nPM molecules were compared with each other and with those of acetylacetone (AA) and benzoylacetone (BA). The single crystal X-ray structure of 4PM confirmed that the tautomer with the OH group next to the pyridine ring best describes the structure in the solid-state. The vibrational bands of the title molecules were assigned to the corresponding normal modes, and the equilibrium between the two cis enol tautomers was estimated by means of IR, Raman and UV/Vis spectroscopy.",
keywords = "1-(n-Pyridinyl)butane-1,3-diones, Intramolecular hydrogen bonding, Tautomerism, UV/Vis spectroscopy, Vibrational spectra, X-ray crystal structure",
author = "Mohammad Vakili and Vahidreza Darugar and Kamounah, {Fadhil S.} and {Erik Hansen}, Poul and Mathias Hermann and Michael Pittelkow",
note = "Publisher Copyright: {\textcopyright} 2023 Elsevier B.V.",
year = "2023",
doi = "10.1016/j.molliq.2023.122074",
language = "English",
volume = "383",
journal = "Journal of Molecular Liquids",
issn = "0167-7322",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Tautomerism in pyridinyl methyl β-diketones in the liquid and the solid state; a combined computational and experimental study

AU - Vakili, Mohammad

AU - Darugar, Vahidreza

AU - Kamounah, Fadhil S.

AU - Erik Hansen, Poul

AU - Hermann, Mathias

AU - Pittelkow, Michael

N1 - Publisher Copyright: © 2023 Elsevier B.V.

PY - 2023

Y1 - 2023

N2 - Three 1-(n-pyridinyl)butane-1,3-diones (nPM) (n = 2, 3, and 4) molecules were synthesized and their molecular structure, tautomerism, conformational stability, and intramolecular hydrogen bonding (IHB) of cis-enol forms, was investigated by a combination of computational and experimental methods. Density functional theory (DFT) calculations were used and the Atoms in Molecules (AIM) analysis indicated an intramolecular hydrogen bond strength as 17.9–20.3 kcal/mol using the B3LYP/6–311++G(d,p) level of theory. The calculated structures, NBO, and intramolecular hydrogen bond strengths for the stable cis-enol forms of nPM molecules were compared with each other and with those of acetylacetone (AA) and benzoylacetone (BA). The single crystal X-ray structure of 4PM confirmed that the tautomer with the OH group next to the pyridine ring best describes the structure in the solid-state. The vibrational bands of the title molecules were assigned to the corresponding normal modes, and the equilibrium between the two cis enol tautomers was estimated by means of IR, Raman and UV/Vis spectroscopy.

AB - Three 1-(n-pyridinyl)butane-1,3-diones (nPM) (n = 2, 3, and 4) molecules were synthesized and their molecular structure, tautomerism, conformational stability, and intramolecular hydrogen bonding (IHB) of cis-enol forms, was investigated by a combination of computational and experimental methods. Density functional theory (DFT) calculations were used and the Atoms in Molecules (AIM) analysis indicated an intramolecular hydrogen bond strength as 17.9–20.3 kcal/mol using the B3LYP/6–311++G(d,p) level of theory. The calculated structures, NBO, and intramolecular hydrogen bond strengths for the stable cis-enol forms of nPM molecules were compared with each other and with those of acetylacetone (AA) and benzoylacetone (BA). The single crystal X-ray structure of 4PM confirmed that the tautomer with the OH group next to the pyridine ring best describes the structure in the solid-state. The vibrational bands of the title molecules were assigned to the corresponding normal modes, and the equilibrium between the two cis enol tautomers was estimated by means of IR, Raman and UV/Vis spectroscopy.

KW - 1-(n-Pyridinyl)butane-1,3-diones

KW - Intramolecular hydrogen bonding

KW - Tautomerism

KW - UV/Vis spectroscopy

KW - Vibrational spectra

KW - X-ray crystal structure

U2 - 10.1016/j.molliq.2023.122074

DO - 10.1016/j.molliq.2023.122074

M3 - Journal article

AN - SCOPUS:85159854338

VL - 383

JO - Journal of Molecular Liquids

JF - Journal of Molecular Liquids

SN - 0167-7322

M1 - 122074

ER -

ID: 356893300