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Application of 17 O Chemical Shift Substitution Parameters to D ‐Hexopyranoses. Correlation between the 17 O and 13 C Chemical Shifts at the Anomeric Centre
Author(s) -
Schulte J.,
Lauterwein J.
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199607)34:7<527::aid-omr915>3.0.co;2-k
Subject(s) - chemistry , anomer , chemical shift , ether , stereochemistry , linear correlation , aldose , mannose , galactose , organic chemistry , glycoside , statistics , mathematics
Abstract 17 O chemical shift substitution parameters obtained previously from the investigation of the conformationally rigid 1,6‐anhydro‐β‐ D ‐hexopyranoses were applied to five α,β‐ D ‐hexopyranoses: allose, glucose, mannose, gulose and galactose. The 17 O chemical shifts predicted for the endocyclic ether oxygens, and also for the anomeric hydroxyl oxygens, were in good agreement with the experimental data. For the anomeric carbons and hydroxyl oxygens the 13 C and 17 O chemical shift differences between α‐ and β‐ D ‐hexopyranoses showed a linear relationship.