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Prebiotic‐Like Condensations of Cyanamide and Glyoxal: Revisiting Intractable Biotars
Author(s) -
Lavado Nieves,
Escamilla Juan Carlos,
Ávalos Martín,
Babiano Reyes,
Cintas Pedro,
Jiménez José Luis,
Palacios Juan Carlos
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601999
Subject(s) - cyanamide , glyoxal , chemistry , molecule , condensation , abiogenesis , chemical evolution , astrobiology , chemical physics , computational chemistry , organic chemistry , physics , astrophysics , stars , thermodynamics
Abstract We report a detailed investigation into the nature of products that are generated by the reactions of cyanamide and glyoxal, two small molecules of astrochemical and prebiotic significance, under different experimental conditions. The experimental data suggest that the formation of oligomeric structures is related in part to the formation of insoluble tholins in the presence of oxygen‐containing molecules. Although oligomerization proceeds well in water, product isolation turned out to be impractical. Instead, solid precipitates were obtained easily in acetone. Crude mixtures have been thoroughly scrutinized by spectroscopic methods, in particular NMR and mass spectroscopy (ESI mode), which are all consistent with the generation of a few functional groups that are embedded into regular chains of five‐ and six‐membered rings, thereby pointing to a supramolecular organization. Three different models of cross‐condensation and chain growth are suggested. These synthetic explorations provide further insights into the formation of complex organic matter in interstellar scenarios and extraterrestrial bodies that might have played a pivotal role in chemical evolution.