Deuterium-induced isotope effects on the ¹³C chemical shifts of α- D -glucose pentaacetate

1,2,3,4,6-Penta-O-acetyl-α-d-glucopyranose and the corresponding [1-²H], [2-²H], [3-²H], [4-²H], [5-²H], and [6,6-²H₂]-labeled compounds were prepared for measuring deuterium/hydrogen-induced effects on ¹³C chemical shift ⁿΔ (DHIECS) values. A conformational analysis of the nondeuterated compound was achieved using density functional theory (DFT) molecular models that allowed calculation of several structural properties as well as Boltzmann-averaged ¹³C NMR chemical shifts by using the gauge-including atomic orbital method. It was found that the DFT-calculated C-H bond lengths correlate with ¹Δ DHIECS.