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Substituent‐induced chemical shifts of aromatic carbon centres in a series of non‐acetylated and peracetylated Para ‐substituted aryl 2‐ N ‐acetamido‐2‐deoxy‐β‐D‐glucopyranosides
Author(s) -
Roy René,
Tropper François D.,
Williams Antony J.
Publication year - 1995
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/mrc.1260331208
Subject(s) - chemistry , substituent , chemical shift , aryl , acetylation , stereochemistry , medicinal chemistry , organic chemistry , computational chemistry , alkyl , biochemistry , gene
The additive behaviour generally observed for the substituent‐induced chemical shifts (SCS) for disubstituted benzenes was examined for a series of aryl 2‐ N ‐acetamido‐2‐deoxy‐β‐D‐glucopyranosides having a wide range of para substituents with varying possible electronic contributions. The SCS values associated with non‐acetylated and peracetylated glucoside rings in para ‐substituted aryl 2‐ N ‐acetamido‐2‐deoxy‐β‐D‐glucopyranosides were calculated. The additive nature of SCS analysis for para ‐substituted systems was shown to hold for the meta and para positions but the very small change in chemical shifts for the ortho positions precluded attempts at analysis of these data. The observation of a good correlation for the ipso carbons for the acetylated compounds compared with a poor correlation for the same site in the non‐acetylated compounds is not well understood.