Differentiation of Rubidiated Methyl-D-Glycoside Stereoisomers by Infrared Multiple-Photon Dissociation Spectroscopy in the O-H and C-H Stretching Regions

作者:Pearson Wright L; Contreras Cesar Cesar; Powell David; Berden Giel; Oomens Jos; Bendiak Brad; Eyler John R*
来源:Journal of Physical Chemistry B, 2015, 119(41): 12970-12981.
DOI:10.1021/acs.jpcb.5b06563

摘要

Four isomeric sugar methylglycosides (alpha- and beta-D-gluco- and galactopyranosides) were evaluated as rubidium cation coordination adducts in the gas phase using variable-wavelength multiple-photon dissociation in the range from 2750 to 3750 cm(-1). The adducts dissociated following photon absorption to yield neutral sugars and the rubidium cation, resulting in infrared "action" spectra. Well-resolved hydroxyl stretching bands clearly differentiate stereoisomers that vary solely in their asymmetry at single carbons. Density functional theory calculations of the lowest-energy gas-phase complexes indicate that rubidium coordinates with lone pairs of oxygen atoms as either bi- or tridentate complexes and that more than one positional coordination isomer could adequately account for most of the O-H stretch frequencies observed for each methylglycoside.

  • 出版日期2015-10-15