1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid

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...

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Autores principales: Mardyukov, Artur, Eckhardt, André K., Schreiner, Peter R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154680/
https://www.ncbi.nlm.nih.gov/pubmed/31899845
http://dx.doi.org/10.1002/anie.201915646
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author Mardyukov, Artur
Eckhardt, André K.
Schreiner, Peter R.
author_facet Mardyukov, Artur
Eckhardt, André K.
Schreiner, Peter R.
author_sort Mardyukov, Artur
collection PubMed
description 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.
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spelling pubmed-71546802020-04-14 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid Mardyukov, Artur Eckhardt, André K. Schreiner, Peter R. Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2020-02-12 2020-03-27 /pmc/articles/PMC7154680/ /pubmed/31899845 http://dx.doi.org/10.1002/anie.201915646 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Mardyukov, Artur
Eckhardt, André K.
Schreiner, Peter R.
1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title_full 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title_fullStr 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title_full_unstemmed 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title_short 1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid
title_sort 1,1‐ethenediol: the long elusive enol of acetic acid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154680/
https://www.ncbi.nlm.nih.gov/pubmed/31899845
http://dx.doi.org/10.1002/anie.201915646
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