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Archean geochemistry of formaldehyde and cyanide and the oligomerization of cyanohydrinThe sources and speciation of reduced carbon and nitrogen inferred for the early Archean are reviewed in terms of current observations and models, and known chemical reactions. Within this framework hydrogen cyanide and cyanide ion in significant concentration would have been eliminated by reaction with excess formaldehyde to form cyanohydrin (glycolonitrile), and with ferrous ion to formferrocyanide. Natural reactions of these molecules would under such conditions deserve special consideration in modeling of primordial organochemical processes. As a step in this direction, transformation reactions have been investigated involving glycolonitrile in the presence of water. We find that glycolonitrile, formed from formaldehyde and hydrogen cyanide or cyanide ion, spontaneously cyclodimerizes to 4-amino-2-hydroxymethyloxazole. The crystalline dimer is the major product at low temperatue (approximately 0 C); the yield diminishes with increasing temperature at the expense of polymerization and hydrolysis products. Hydrolysis of glycolamide and of oxazole yields a number of simpler organic molecules, including ammonia and glycolamide. The spontaneous polymerization of glycolonitrile and its dimer gives rise to soluble, cationic oligomers of as yet unknown structure, and, unless arrested, to a viscous liquid, insoluble in water. A loss of cyanide by reaction with formaldehyde, inferred for the early terrestrial hydrosphere and cryosphere would present a dilemma for hypotheses invoking cyanide and related compounds as concentrated reactants capable of forming biomolecular precursor species. Attempts to escape from its horns may take advantage of the efficient concentration and separation of cyanide as solid ferriferrocyanide, and most directly of reactions of glycolonitrile and its derivatives.
Document ID
19940038829
Acquisition Source
Legacy CDMS
Document Type
Reprint (Version printed in journal)
External Source(s)
Authors
Arrhenius, T.
(Cytel Corporation La Jolla, CA, United States)
Arrhenius, G.
(Univ. of California, San Diego, CA United States)
Paplawsky, W.
(Univ. of California, San Diego, CA United States)
Date Acquired
August 16, 2013
Publication Date
February 1, 1994
Publication Information
Publication: Origins of Life and Evolution of the Biosphere
Volume: 24
Issue: 1
ISSN: 0169-6149
Subject Category
Geophysics
Accession Number
94A62278
Funding Number(s)
CONTRACT_GRANT: NAGW-2881
CONTRACT_GRANT: NSF-87-21219
CONTRACT_GRANT: NAGW-1031
Distribution Limits
Public
Copyright
Other

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