Preparation and characterization of the enol of acetamide: 1-aminoethenol, a high-energy prebiotic molecule.

Chemical Science
Artur MardyukovPeter R Schreiner

Abstract

Amide tautomers, which constitute the higher-energy amide bond linkage, not only are key for a variety of biological but also prebiotic processes. In this work, we present the gas-phase synthesis of 1-aminoethenol, the higher-energy tautomer of acetamide, that has not been spectroscopically identified to date. The title compound was prepared by flash vacuum pyrolysis of malonamic acid and was characterized employing matrix isolation infrared as well as ultraviolet/visible spectroscopy. Coupled-cluster computations at the AE-CCSD(T)/cc-pVTZ level of theory support the spectroscopic assignments. Upon photolysis at λ > 270 nm, the enol rearranges to acetamide as well as ketene and ammonia. As the latter two are even higher in energy, they constitute viable starting materials for formation of the title compound.

References

Sep 22, 1998·Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life·W M Irvine
Jul 27, 1990·Science·C F ChybaC Sagan
Oct 25, 2001·The Journal of Organic Chemistry·Annette D. Allen, Thomas T. Tidwell
Mar 29, 2002·Nature·G M Muñoz CaroJ M Greenberg
Aug 21, 2002·Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life·Akira Shimoyama, Ryo Ogasawara
Nov 15, 2002·Journal of the American Chemical Society·Austin W ActonBrian D Wagner
Aug 9, 2003·Journal of the American Chemical Society·Xue-Bo ChenDe-Cai Fang
Jul 31, 1959·Science·S L MILLER, H C UREY
Jan 13, 2004·Science·A RicardoS A Benner
Feb 22, 2007·Physical Chemistry Chemical Physics : PCCP·Fabrice DuvernayThierry Chiavassa
Apr 20, 2007·Chemistry & Biodiversity·André Brack
Jun 13, 2008·Nature·Peter R SchreinerAttila G Császár
May 11, 2011·Journal of the American Chemical Society·Hyo-Joong KimSteven A Benner
Aug 13, 2011·Proceedings of the National Academy of Sciences of the United States of America·Michael P CallahanJason P Dworkin
Mar 10, 2012·Organic & Biomolecular Chemistry·David LeyPeter R Schreiner
Nov 1, 2013·Chemical Reviews·Kepa Ruiz-MirazoAndrés de la Escosura
Mar 25, 2017·Nature Chemistry·Adam J Coggins, Matthew W Powner
Feb 13, 2018·Angewandte Chemie·André K Eckhardt, Peter R Schreiner
Sep 12, 2018·Nature Chemistry·André K EckhardtPeter R Schreiner
Nov 9, 2018·Nature·Bénédicte MénezMatthieu Réfrégiers
Mar 1, 2019·Chemical Society Reviews·Chris R ArumainayagamPeter J Hodge
Nov 20, 2019·Proceedings of the National Academy of Sciences of the United States of America·Yoshihiro FurukawaTomoki Nakamura
Jan 4, 2020·Angewandte Chemie·Artur MardyukovPeter R Schreiner

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Citations

Apr 30, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·N Fabian Kleimeier, Ralf I Kaiser
May 6, 2021·Angewandte Chemie·Artur MardyukovPeter R Schreiner
Jun 26, 2021·Chemical Science·Zachary R JonesDavid H Woen
Aug 11, 2021·The Journal of Physical Chemistry. a·Bastian BernhardtPeter R Schreiner
Aug 20, 2021·Journal of the American Chemical Society·N Fabian KleimeierRalf I Kaiser

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Methods Mentioned

BETA
NMR
deamination

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