SUBSTITUENT-INDUCED CHEMICAL-SHIFTS OF AROMATIC CARBON CENTERS IN A SERIES OF NON-ACETYLATED AND PERACETYLATED PARASUBSTITUTED ARYL 2-N-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES
R. Roy et al., SUBSTITUENT-INDUCED CHEMICAL-SHIFTS OF AROMATIC CARBON CENTERS IN A SERIES OF NON-ACETYLATED AND PERACETYLATED PARASUBSTITUTED ARYL 2-N-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES, Magnetic resonance in chemistry, 33(12), 1995, pp. 981-984
The additive behaviour generally observed for the substituent-induced
chemical shifts (SCS) for disubstituted benzenes was examined for a se
ries of aryl 2-N-acetamido-2-deoxy-beta-D-glucopyranosides having a wi
de range of para substituents with varying possible electronic contrib
utions. The SCS values associated with nonacetylated and peracetylated
glucoside rings in para-substituted aryl 2-N-acetamido-2-deoxy-beta-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 p
ositions precluded attempts at analysis of these data. The observation
of a good correlation for the ipso carbons for the acetylated compoun
ds compared with a poor correlation for the same site in the non-acety
lated compounds is not well understood.