Related Products of 1824-94-8. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol, is researched, Molecular C7H14O6, CAS is 1824-94-8, about Gas phase dynamics, conformational transitions and spectroscopy of charged saccharides: the oxocarbenium ion, protonated anhydrogalactose and protonated methyl galactopyranoside. Author is Dvores, M. P.; Carcabal, P.; Maitre, P.; Simons, J. P.; Gerber, R. B..
Protonated intermediates are postulated to be involved in the rate determining step of many sugar reactions. This paper presents a study of protonated sugar species, isolated in the gas phase, using a combination of IR multiple photon dissociation (IRMPD) spectroscopy, classical ab initio mol. dynamics (AIMD) and quantum mech. vibrational SCF (VSCF) calculations It provides a likely identification of the reactive intermediate oxocarbenium ion structure in a D-galactosyl system as well as the saccharide pyrolysis product anhydrogalactose (that suggests oxocarbenium ion stabilization), along with the spectrum of the protonated parent species: Me D-galactopyranoside-H+. Its vibrational fingerprint indicates intramol. proton sharing. Classical AIMD simulations for galactosyl oxocarbenium ions, conducted in the temperature range ∼300-350 K (using B3LYP potentials on-the-fly) reveal efficient transitions on the picosecond timescale. Multiple conformers are likely to exist under the exptl. conditions and along with static VSCF calculations, they have facilitated the identification of the individual structural motifs of the galactosyl oxocarbenium ion and protonated anhydrogalactose ion conformers that contribute to the observed exptl. spectra. These results demonstrate the power of exptl. IRMPD spectroscopy combined with dynamics simulations and with computational spectroscopy at the anharmonic level to unravel conformer structures of protonated saccharides, and to provide information on their lifetimes.
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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate