The keto/enol tautomerism in acetoacetyl fluoride: properties, spectroscopy, and gas-phase and crystal structures of the enol form
Literature Information
Natalya V. Belova, Heinz Oberhammer, Xiaoqing Zeng, Michael Gerken, Helge Willner, Raphael J. F. Berger, Stuart A. Hayes, Norbert W. Mitzel
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.
Related Literature
A very sensitive high-resolution NMR method for quadrupolar nuclei: SPAM-DQF-STMAS
Jean-Paul Amoureux, Alexandrine Flambard, Laurent Delevoye, Lionel Montagne
DOI: 10.1039/B502840J
Well-defined imidotitanium alkyl cations: agostic interactions, migratory insertion vs.[2+2] cycloaddition, and the first structurally authenticated AlMe3 adduct of any transition metal alkyl cation
Paul D. Bolton, Eric Clot, Andrew R. Cowley, Philip Mountford
DOI: 10.1039/B504567C
Reversible ferromagnetic–antiferromagnetic transformation upon dehydration–hydration of the nanoporous coordination framework, [Co3(OH)2(C4O4)2]·3H2O
Mohamedally Kurmoo, Hitoshi Kumagai, Karena W. Chapman, Cameron J. Kepert
DOI: 10.1039/B500614G
A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade
Charlotte M. Haskins, David W. Knight
DOI: 10.1039/B417625C
Responsive lanthanide luminescent cyclen complexes: from switching/sensing to supramolecular architectures
DOI: 10.1039/B418196D
Stereodifferentiation in the formation and decay of the encounter complex in bimolecular electron transfer with photoactivated acceptors
Julia Pérez-Prieto, Raquel E. Galian, Maria C. Morant-Miñana, Miguel A. Miranda
DOI: 10.1039/B500697J
Synthesis, characterization and FET properties of novel dithiazolylbenzothiadiazole derivatives
Md. Akhtaruzzaman, Naoto Kamata, Jun-ichi Nishida, Shinji Ando, Hirokazu Tada, Masaaki Tomura, Yoshiro Yamashita
DOI: 10.1039/B503814F
Photoinduced DNA end capping viaN3-methyl-5-cyanovinyl-2′-deoxyuridine
Yoshinaga Yoshimura, Tadayoshi Ikemoto, Akio Nakazawa, Masayuki Hayashi, Isao Saito
DOI: 10.1039/B504162G
Porous materials show superhydrophobic to superhydrophilic switching
Neil J. Shirtcliffe, Glen McHale, Michael I. Newton, Carole C. Perry, Paul Roach
DOI: 10.1039/B502896E
Organometallic based strategies for metal nanocrystal synthesis
DOI: 10.1039/B501835H
You might also like
How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?
2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...
Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?
2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...
What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?
When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...
What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?
When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?
3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...
What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?
(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...
What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?
Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...
Source Journal
Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.












![5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure 5-Bromo-3-isopropyl-1H-pyrrolo[2,3-b]pyridine structure](https://static.chemtradehub.com/structs/125/1256819-54-1-8620.webp)

