Issue 37, 2010

The keto/enol tautomerism in acetoacetyl fluoride: properties, spectroscopy, and gas-phase and crystal structures of the enol form

Abstract

Tautomeric properties of acetoacetyl fluoride, CH3–C(O)–CH2–C(O)–F, were studied by IR (gas phase), Raman (liquid and solid), and NMR spectroscopy (neat liquid), gas electron diffraction (GED), X-ray crystallography, and quantum chemical calculations. The keto-enol tautomer possesses a much higher vapour pressure than the diketo form and therefore the keto-enol form strongly predominates in the gas phase. In the neat liquid state the thermally unstable compound tautomerizes at low temperatures slowly to yield the diketo form. Raman and NMR spectra show equilibrium with strong predominance of the diketo tautomer (>90%) in the liquid phase. Single crystals, grown at −90 °C from the gas phase, contain exclusively acetoacetyl fluoride in the keto-enol form and the molecules possess a planar skeleton with overall CS symmetry and with the O–H bond adjacent to the methyl group.

Graphical abstract: The keto/enol tautomerism in acetoacetyl fluoride: properties, spectroscopy, and gas-phase and crystal structures of the enol form

Supplementary files

Article information

Article type
Paper
Submitted
09 Feb 2010
Accepted
28 May 2010
First published
03 Aug 2010

Phys. Chem. Chem. Phys., 2010,12, 11445-11453

The keto/enol tautomerism in acetoacetyl fluoride: properties, spectroscopy, and gas-phase and crystal structures of the enol form

N. V. Belova, H. Oberhammer, X. Zeng, M. Gerken, H. Willner, R. J. F. Berger, S. A. Hayes and N. W. Mitzel, Phys. Chem. Chem. Phys., 2010, 12, 11445 DOI: 10.1039/C002743J

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