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Two unexpected effects found with 2,3,4,6-Tetra-O-methyl-D-Gluco- and mannopyranosyl oxacarbenium ions: an O-2 pseudoequatorial preference and a large H-2-C-2--O-2-CH3syn preference

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1021/bk-2006-0930.ch017
AuthorSearch for: ; Search for: 1; Search for: 1; Search for: ; Search for: 2
Affiliation
  1. National Research Council Canada. NRC Steacie Institute for Molecular Sciences
  2. National Research Council Canada
FormatText, Book Chapter
Abstract
Analysis of two of the stable conformations (B0 and B1) of a number of differently configured glycopyranosyl oxacarbenium ions by Density Functional Theory (DFT)calculations found two unexpected phenomena. Firstly, a marked preference for O-2 to be pseudo-equatorial that most dramatically leads to the B1 conformation of D-gluco configured cations taking a 5S1 conformation. The second phenomenon is that the H-2-C-2-O-2-CH3 torsion angle is found to prefer syn conformations over anti conformations by more than 10 kJ mol-1. Preliminary analysis of these two effects by examining the geometric consequences, the LUMO's and by Natural Bond Order (NBO) analysis are presented.
Publication date
PublisherAmerican Chemical Society
In
  • NMR Spectroscopy and Computer Modeling of Carbohydrates (9 March 2006): 302–319.
Series
  • ACS Symposium Series, no. 930.
LanguageEnglish
Peer reviewedYes
NRC numberLONESCU2005
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Record identifierc5117b23-d401-4bdf-a965-0e34be27a9ec
Record created2009-07-10
Record modified2020-06-16
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