Formation of glycine from HCN and H2O: A computational mechanistic study

[Display omitted] •Theoretical (CBS-QB3) reaction pathways for the formation of glycine.•Two pathways for amino malononitrile monoamide+2H2O→glycine+HNCO+NH3.•The pathway involving an amino ketone was much more favored.•Addition of a catalytic H2O greatly enhanced steps occurring by H rearrangement....

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Bibliographic Details
Published in:Chemical physics letters 2017-05, Vol.675, p.6-10
Main Authors: Lee, Hyun Moo, Choe, Joong Chul
Format: Article
Language:English
Subjects:
Astrobiology
Astrophysics
CBS calculation
Prebiotic chemistry
Reaction pathway
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Summary:[Display omitted] •Theoretical (CBS-QB3) reaction pathways for the formation of glycine.•Two pathways for amino malononitrile monoamide+2H2O→glycine+HNCO+NH3.•The pathway involving an amino ketone was much more favored.•Addition of a catalytic H2O greatly enhanced steps occurring by H rearrangement. The potential energy surfaces for the formation of glycine from HCN and H2O were determined from CBS-QB3 calculations. After the formation of a HCN trimer, amino malononitrile, amino malononitrile monoamide (3) was formed by a water addition reaction. Two pathways were found for the subsequent reaction, 3+2H2O→glycine+HNCO+NH3. One pathway involving an amino ketone was much more favored than the other pathway involving glycinamide. Addition of a water molecule as a catalyst greatly enhanced steps occurring by hydrogen rearrangement.
ISSN:0009-2614
1873-4448
DOI:10.1016/j.cplett.2017.02.079