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‐ 2 H], [2‐ 2 H], [3‐ 2 H], [4‐ 2 H], [5‐ 2 H], and [6,6‐ 2 H 2 ]‐labeled compounds were prepared for measuring deuterium/hydrogen‐induced effects on 13 C chemical shift n Δ (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 13 C NMR chemical shifts by using the gauge‐including atomic orbital method. It was found that the DFT‐calculated C–H bond lengths correlate with 1 Δ DHIECS. Copyright © 2013 John Wiley & Sons, Ltd.