Chemical shifts of carbohydrates

✍ Scribed by L.D. Hall

• Book ID: 104240778
• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 180 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89511-3

✦ Synopsis

In their study of six-membered ring compounds by nuclear magnetic resonance (N.W.R.) spectroscopy, Lemieux, Kullnig, Schneider and Bernstein1 reported the first observation of chemical shifts which could be attributed solely to changes in molecular gecmetry. Evidence frm fully acetylated pyranose carbohydrates lead to the conclusion that axial protons resonate at higher field (T-value) than their equatorial counterparts. Since then comparatively few attempts %3,'+ have been made within carbohydrate chemistry to place this observation on a theoretical basis.

We have now measurad the N.M.R. spectra of free pentoses and hexoses in D20 and remeasured the spectra of fully aeetylated sugars in CHCl, solution. The ancmeric protons gave the only resolved multiplets and inspection of their chemical shifts shown in the Table indicates that these shifts are largely dependent on the configuration at C2 and are only slightly, although