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1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
Author(s) -
Mardyukov Artur,
Eckhardt André K.,
Schreiner Peter R.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915646
Subject(s) - enol , acetic acid , ketene , tautomer , chemistry , pyrolysis , photochemistry , malonic acid , spectroscopy , photodissociation , keto–enol tautomerism , organic chemistry , catalysis , physics , quantum mechanics
We present the first spectroscopic identification of hitherto unknown 1,1‐ethenediol, the enol tautomer of acetic acid. The title compound was generated in the gas phase through flash vacuum pyrolysis of malonic acid at 400 °C. The pyrolysis products were subsequently trapped in argon matrices at 10 K and characterized spectroscopically by means of IR and UV/Vis spectroscopy together with matching its spectral data with computations at the CCSD(T)/cc‐pCVTZ and B3LYP/6–311++G(2d,2p) levels of theory. Upon photolysis at λ =254 nm, the enol rearranges to acetic acid and ketene.