Formation of acetamide in interstellar medium

Foo, Lois; Surányi, Attila; Guljas, Andrea; Szőri, Milán; Villar, John Justine S.; Viskolcz, Béla; Csizmadia, Imre G.; Rágyanszki, Anita; Fiser, Béla

doi:10.1016/j.molap.2018.06.002

Cited by 16 publications

(29 citation statements)

References 24 publications

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“…Eight bimolecular reaction paths were suggested that could lead to the formation of acetamide. 1-Aminoethenol (1), the tautomer of acetamide (3, Scheme 1), has been suggested to be a key intermediate for the formation of 3 in the ISM, 37 but has never been observed. To date, only indirect evidence for the experimental preparation of 1 38,39 and its enolate 40 in the gas phase comes from mass spectrometric experiments; there are no spectroscopic data available for 1.…”

Section: Introductionmentioning

confidence: 99%

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

2020

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Section: Introductionmentioning

confidence: 99%

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

2020

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“…These rearrangement reactions as well as other synthesis reactants were eliminated because of unviability due to the lack of formation of pi bonds, lack of breakdown of sigma bonds, or excessive free energy values 17,18 . Based on the sources of energy available in ISM, any larger molecules would not break down into acetamide as molecules greater than 9 atoms of this complexity are less frequently found in ISM 19,20 . These molecules, containing oxygen, carbon, hydrogen, and nitrogen, usually exist only as polymers 19,20 .…”

Section: Resultsmentioning

confidence: 99%

“…Based on the sources of energy available in ISM, any larger molecules would not break down into acetamide as molecules greater than 9 atoms of this complexity are less frequently found in ISM 19,20 . These molecules, containing oxygen, carbon, hydrogen, and nitrogen, usually exist only as polymers 19,20 . The most likely synthesis came from ketene and ammonia, and structures were located and visually confirmed by intramolecular motions created by frequencies made in GaussView software 21 .…”

Section: Resultsmentioning

confidence: 99%

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Ketene and Ammonia Forming Acetamide in the Interstellar Medium

Kothari

Zhu

Babi

et al. 2020

J Undergrad Life Sci

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Background: Peptide bonds are among the fundamental building blocks of life, polymerizing amino acids to form proteins that make up the structural components of living cells and regulate biochemical processes. The detection of glycine by NASA in comet Wild 2 in 2009 suggests the possibility of the formation of biomolecules in extraterrestrial environments through the interstellar medium. Detected in the dense molecular cloud Sagittarius B2, acetamide is the largest molecule containing a peptide bond and is hypothesized to be the precursor to all amino acids; as such, viability of its formation is of important biological relevance. Methods: Under a proposed mechanism of ammonia and ketene reactants, which have also been detected in dense molecular clouds in the ISM, the reaction pathway for the formation of acetamide was modelled using quantum chemical calculations in Gaussian16, using Austin-Frisch-Petersson functional with dispersion density functional theory at a 6-31G(d) basis set level of theory to optimize geometries and determine the thermodynamic properties for the reaction. Stability of the reactants, transition states, and products were examined to establish a reasonable mechanism. Conclusion: Product formation of acetamide was found to be highly exergonic and exothermic with a low energy barrier, suggesting a mechanism that is viable in the extreme density and temperature conditions found in ISM.

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“… [12] The tautomers of acetamide and acetic acid, 1‐aminoethenol [13] and 1,1‐ethenediol, [14] respectively, whose structures have only very recently been identified, are deemed to be key intermediates in the organic chemistry of space. [15] …”

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

2021

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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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Formation of acetamide in interstellar medium

Cited by 16 publications

References 24 publications

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

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

Ketene and Ammonia Forming Acetamide in the Interstellar Medium

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

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