Solvent effects on the photochemistry of 4-aminoimidazole-5-carbonitrile, a prebiotically plausible precursor of purines

0435971 - BFÚ 2015 RIV GB eng J - Journal Article
Szabla, Rafal - Šponer, Judit E. - Šponer, Jiří - Sobolewski, A. L. - Gora, R.W.
Solvent effects on the photochemistry of 4-aminoimidazole-5-carbonitrile, a prebiotically plausible precursor of purines.
Physical Chemistry Chemical Physics. Roč. 16, č. 33 (2014), s. 17617-17626. ISSN 1463-9076. E-ISSN 1463-9084
R&D Projects: GA ČR(CZ) GA14-12010S
Institutional support: RVO:68081707
Keywords : PROTON-TRANSFER PROCESSES * INDOLE-WATER CLUSTERS * CHEMICAL EVOLUTION
Subject RIV: BO - Biophysics
Impact factor: 4.493, year: 2014

4-Aminoimidazole-5-carbonitrile (AICN) was suggested as a prebiotically plausible precursor of purine nucleobases and nucleotides. Although it can be formed in a sequence of photoreactions, AICN is immune to further irradiation with UV-light. We present state-of-the-art multi-reference quantum-chemical calculations of potential energy surface cuts and conical intersection optimizations to explain the molecular mechanisms underlying the photostability of this compound. We have identified the N-H bond stretching and ring-puckering mechanisms that should be responsible for the photochemistry of AICN in the gas phase. We have further considered the photochemistry of AICN-water clusters, while including up to six explicit water molecules.
Permanent Link: http://hdl.handle.net/11104/0239816