1,1‐Ethendiol – Das lange Zeit schwer fassbare Enol der Essigsäure

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 8C 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 l = 180-254 nm, 1,1,2-ethenetriol rearranges to glycolic acid and ketene.

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1,1,2‐Ethenetriol: The Enol of Glycolic Acid, a High‐Energy Prebiotic Molecule

Mardyukov

Keul

Schreiner

2021

Angewandte Chemie

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Prebiotic Synthesis and Isomerization in Interstellar Analog Ice: Glycinal, Acetamide, and Their Enol Tautomers

et al. 2023

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Glycinal (HCOCH2NH2) and acetamide (CH3CONH2) are simple molecular building blocks of biomolecules in prebiotic chemistry, though their origin on early Earth and formation in interstellar media remain a mystery. These molecules are formed with their tautomers in low temperature interstellar model ices upon interaction with simulated galactic cosmic rays. Glycinal and acetamide are accessed via barrierless radical‐radical reactions of vinoxy (⋅CH2CHO) and acetyl (⋅C(O)CH3), and then undergo keto‐enol tautomerization. Exploiting tunable photoionization reflectron time‐of‐flight mass spectroscopy and photoionization efficiency (PIE) curves, these results demonstrate fundamental reaction pathways for the formation of complex organics through non‐equilibrium ice reactions in cold molecular cloud environments. These molecules demonstrate an unconventional starting point for abiotic synthesis of organics relevant to contemporary biomolecules like polypeptides and cell membranes in deep space.

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1,1,2‐Ethenetriol: The Enol of Glycolic Acid, a High‐Energy Prebiotic Molecule

2021

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1,1‐Ethendiol – Das lange Zeit schwer fassbare Enol der Essigsäure

Cited by 6 publications

References 60 publications

1,1,2‐Ethenetriol: The Enol of Glycolic Acid, a High‐Energy Prebiotic Molecule

1,1,2‐Ethenetriol: The Enol of Glycolic Acid, a High‐Energy Prebiotic Molecule

Prebiotic Synthesis and Isomerization in Interstellar Analog Ice: Glycinal, Acetamide, and Their Enol Tautomers

1,1,2‐Ethenetriol: The Enol of Glycolic Acid, a High‐Energy Prebiotic Molecule

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