Ice chemistry of acetaldehyde reveals competitive reactions in the first step of the Strecker synthesis of alanine: Formation of HO-CH(CH<inf>3</inf>)-NH<inf>2</inf> vs. HO-CH(CH<inf>3</inf>)-CN

Aurélien Fresneau, Grégoire Danger, Albert Rimola, Fabrice Duvernay, Patrice Theulé, Thierry Chiavassa

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Abstract

© 2015 The Authors. Published by Oxford University Press on behalf of the Royal Astronomical Society. The understanding of compound formation in laboratory simulated astrophysical environments is an important challenge in obtaining information on the chemistry occurring in these environments. We here investigate by means of both laboratory experiments and quantum chemical calculations the ice-based reactivity of acetaldehyde (CH3CHO) with ammonia (NH3) and hydrogen cyanide (HCN) in excess of water (H2O) promoted by temperature. A priori, this study should give information on alanine (2HN-CH(CH3)-COOH) formation (the simplest chiral amino acid detected in meteorites), since these reactions concern the first steps of its formation through the Strecker synthesis. However, infrared spectroscopy, mass spectrometry with HC14N or HC15N isotopologues and B3LYP-D3 results converge to indicate that an H2O-dominated ice containing CH3CHO, NH3 and HCN not only leads to the formation of α-aminoethanol (2HN-CH(CH3)-OH, the product compound of the first step of the Strecker mechanism) and its related polymers (2HN-(CH(CH3)-O)n-H) due to reaction between CH3CHO and NH3, but also to the 2-hydroxypropionitrile (HO-CH(CH3)-CN) and its related polymers (H-(O-CH(CH3))n-CN) from direct reaction between CH3CHO and HCN. The ratio between these two species depends on the initial NH3/HCN ratio in the ice. Formation of α-aminoethanol is favoured when the NH3 concentration is larger than HCN.We also show that the presence of water is essential for the formation of HO-CH(CH3)-CN, contrarily to 2HN-CH(CH3)-OH whose formation also takes place in absence of H2O ice. As in astrophysical ices NH3 is more abundant than HCN, formation of α-aminoethanol should consequently be favoured compared to 2-hydroxypropionitrile, thus pointing out α-aminoethanol as a plausible intermediate species for alanine synthesis through the Strecker mechanism in astrophysical ices.
Original languageEnglish
Pages (from-to)1649-1660
JournalMonthly Notices of the Royal Astronomical Society
Volume451
Issue number2
DOIs
Publication statusPublished - 1 May 2015

Keywords

  • Astrochemistry
  • Comets: general
  • Molecular data
  • Molecular processes

Fingerprint Dive into the research topics of 'Ice chemistry of acetaldehyde reveals competitive reactions in the first step of the Strecker synthesis of alanine: Formation of HO-CH(CH<inf>3</inf>)-NH<inf>2</inf> vs. HO-CH(CH<inf>3</inf>)-CN'. Together they form a unique fingerprint.

Cite this