Adenine formation without HCN

J Phys Chem A. 2014 May 22;118(20):3637-44. doi: 10.1021/jp5018778. Epub 2014 May 12.

Abstract

From a historic point of view adenine was always presumed to be the product of HCN pentamerization. In this work a new mechanism for adenine synthesis in the gas phase without HCN is proposed. The concept of retrosynthetic analysis was employed to create a tautomer of adenine, which can be reached from previously observed interstellar molecules C3NH and HNCNH and its isomer H2NCN. MP2/6-311++G(2d,2p) calculations were performed to calculate the Gibbs free energy of the minimum and the transition state (TS) structures involved in the six step mechanism. This new mechanism requires a smaller number of steps, the reaction energy is twice as exergonic, and the rate determining TS is lower in energy than the corresponding ones proposed elsewhere in the literature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / chemical synthesis*
  • Adenine / chemistry
  • Hydrogen Cyanide / chemistry
  • Quantum Theory

Substances

  • Hydrogen Cyanide
  • Adenine