X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones

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Standard

X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones. / Jørgensen, Flemming S.; Brown, R. S.; Carlsen, Lars; Duus, Fritz.

In: Journal of the American Chemical Society, Vol. 104, No. 22, 01.01.1982, p. 5922-5926.

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

Harvard

Jørgensen, FS, Brown, RS, Carlsen, L & Duus, F 1982, 'X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones', Journal of the American Chemical Society, vol. 104, no. 22, pp. 5922-5926. https://doi.org/10.1021/ja00386a014

APA

Jørgensen, F. S., Brown, R. S., Carlsen, L., & Duus, F. (1982). X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones. Journal of the American Chemical Society, 104(22), 5922-5926. https://doi.org/10.1021/ja00386a014

Vancouver

Jørgensen FS, Brown RS, Carlsen L, Duus F. X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones. Journal of the American Chemical Society. 1982 Jan 1;104(22):5922-5926. https://doi.org/10.1021/ja00386a014

Author

Jørgensen, Flemming S. ; Brown, R. S. ; Carlsen, Lars ; Duus, Fritz. / X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones. In: Journal of the American Chemical Society. 1982 ; Vol. 104, No. 22. pp. 5922-5926.

Bibtex

@article{776179daed554b0aacc124348a26ba96,
title = "X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones",
abstract = "X-ray photoelectron spectroscopy has been used to record the O1s and S2p ionization spectra of thioacetylacetone, 2-acetylcyclohexanethione, 2-thioacetylcyclohexanone, the S-methyl derivative of thioacetylacetone, and propyl 3-mercaptocrotonate in the gas phase. It is shown that both the enol and the enethiol tautomers of the β-thioxoketones can be detected, and the enol/enethiol ratios for thioacetylacetone, 2-acetylcyclohexanethione, and 2-thioacetylcyclohexanone were determined to be 61:39, 30:70, and 80:20, respectively, based on the intensities of the oxygen ionizations. The conclusions derived from the sulfur region support the above, although they are less clear due to sulfur spin-orbit splitting. The enol/enethiol ratios obtained in the gas phase by XPS are compared with data from other methods, showing good agreement between results obtained in the gas phase and in solution. The binding energy (BE) shifts of the O1s and S2p orbitals have been discussed and suggest that geometrical factors affect the strength of the intramolecular hydrogen bond.",
author = "J{\o}rgensen, {Flemming S.} and Brown, {R. S.} and Lars Carlsen and Fritz Duus",
year = "1982",
month = jan,
day = "1",
doi = "10.1021/ja00386a014",
language = "English",
volume = "104",
pages = "5922--5926",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "ACS Publications",
number = "22",

}

RIS

TY - JOUR

T1 - X-ray Photoelectron Spectroscopic Study of the Enol-Enethiol Tautomerism of Thioacetylacetone and Related β-Thioxoketones

AU - Jørgensen, Flemming S.

AU - Brown, R. S.

AU - Carlsen, Lars

AU - Duus, Fritz

PY - 1982/1/1

Y1 - 1982/1/1

N2 - X-ray photoelectron spectroscopy has been used to record the O1s and S2p ionization spectra of thioacetylacetone, 2-acetylcyclohexanethione, 2-thioacetylcyclohexanone, the S-methyl derivative of thioacetylacetone, and propyl 3-mercaptocrotonate in the gas phase. It is shown that both the enol and the enethiol tautomers of the β-thioxoketones can be detected, and the enol/enethiol ratios for thioacetylacetone, 2-acetylcyclohexanethione, and 2-thioacetylcyclohexanone were determined to be 61:39, 30:70, and 80:20, respectively, based on the intensities of the oxygen ionizations. The conclusions derived from the sulfur region support the above, although they are less clear due to sulfur spin-orbit splitting. The enol/enethiol ratios obtained in the gas phase by XPS are compared with data from other methods, showing good agreement between results obtained in the gas phase and in solution. The binding energy (BE) shifts of the O1s and S2p orbitals have been discussed and suggest that geometrical factors affect the strength of the intramolecular hydrogen bond.

AB - X-ray photoelectron spectroscopy has been used to record the O1s and S2p ionization spectra of thioacetylacetone, 2-acetylcyclohexanethione, 2-thioacetylcyclohexanone, the S-methyl derivative of thioacetylacetone, and propyl 3-mercaptocrotonate in the gas phase. It is shown that both the enol and the enethiol tautomers of the β-thioxoketones can be detected, and the enol/enethiol ratios for thioacetylacetone, 2-acetylcyclohexanethione, and 2-thioacetylcyclohexanone were determined to be 61:39, 30:70, and 80:20, respectively, based on the intensities of the oxygen ionizations. The conclusions derived from the sulfur region support the above, although they are less clear due to sulfur spin-orbit splitting. The enol/enethiol ratios obtained in the gas phase by XPS are compared with data from other methods, showing good agreement between results obtained in the gas phase and in solution. The binding energy (BE) shifts of the O1s and S2p orbitals have been discussed and suggest that geometrical factors affect the strength of the intramolecular hydrogen bond.

UR - http://www.scopus.com/inward/record.url?scp=0001708626&partnerID=8YFLogxK

U2 - 10.1021/ja00386a014

DO - 10.1021/ja00386a014

M3 - Journal article

AN - SCOPUS:0001708626

VL - 104

SP - 5922

EP - 5926

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 22

ER -

ID: 218714624