title: Tautomers of Gas-Phase Erythrose and Their Interconversion Reactions: Insights from High-Level ab Initio Study.
abstract: D-Erythrose is a C4 monosaccharide with a biological and potential astrobiological relevance. We have investigated low-energy structures of d-erythrose and their interconversion in the gas phase with the highest-level calculations up-to-date. We have identified a number of structurally distinct furanose and open-chain isomers and predicted α ↔ α and β ↔ β furanose interconversion pathways involving the O-H rotamers. We have estimated relative Gibbs free energies of the erythrose species based on the CCSD(T)/aug-cc-pVTZ electronic energies and MP2/aug-cc-pVTZ vibrational frequencies. By using natural bond orbital theory we have also quantified a stabilization of erythrose conformers and interconversion transition states by intramolecular H-bonds.
authors.affiliation: Faculty of Chemistry, Wroclaw University , F. Joliot-Curie 14, 50-383 Wroclaw, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Szczepaniak
authors.affiliation: Faculty of Chemistry, Wroclaw University , F. Joliot-Curie 14, 50-383 Wroclaw, Poland.
authors.forename: Jerzy
authors.initials: J
authors.lastname: Moc
mesh_terms: D003500:Cyclization; D005740:Gases / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D044367:Phase Transition; D011789:Quantum Theory; D013780:Tetroses / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D005740:Gases; D013780:Tetroses; C073321:erythrose