Journal article

Publication year: 2021

Pages: 15313-15316

Journal: Angewandte Chemie International Edition

Volume number: 60

Issue number: 28

ISSN: 1433-7851

Open access status: Green

DOI Link: https://doi.org/10.1002/anie.202104436

Publisher: Wiley

Abstract: 

As low-temperature conditions (e.g. in space) prohibit reactions requiring large activation energies, an alternative mechanism for follow-up transformations of highly stable molecules involves the reactions of higher energy isomers that were generated in a different environment. Hence, one working model for the formation of larger organic molecules is their generation from high-lying isomers of otherwise rather stable molecules. As an example, we present here the synthesis as well as IR and UV/Vis spectroscopic identification of the previously elusive 1,1,2-ethenetriol, the higher energy enol tautomer of glycolic acid, a rather stable and hence unreactive biological building block. The title compound was generated in the gas phase by flash vacuum pyrolysis of tartronic acid at 400 degrees C and was subsequently trapped in argon matrices at 10 K. The spectral assignments are supported by B3LYP/6-311++G(2d,2p) computations. Upon photolysis at lambda=180-254 nm, 1,1,2-ethenetriol rearranges to glycolic acid and ketene.

Harvard Citation style: Mardyukov, A., Keul, F. and Schreiner, P. (2021) 1,1,2-Ethenetriol: The Enol of Glycolic Acid, a High-Energy Prebiotic Molecule, Angewandte Chemie International Edition, 60(28), pp. 15313-15316. https://doi.org/10.1002/anie.202104436

APA Citation style: Mardyukov, A., Keul, F., & Schreiner, P. (2021). 1,1,2-Ethenetriol: The Enol of Glycolic Acid, a High-Energy Prebiotic Molecule. Angewandte Chemie International Edition. 60(28), 15313-15316. https://doi.org/10.1002/anie.202104436