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

作者：Perez Hernandez Nury; Alvarez Cisneros Celina; Cerda Garcia Rojas Carlos M; Morales Rios Martha S; Joseph Nathan Pedro^*

来源：Magnetic Resonance in Chemistry, 2013, 51(3): 136-142.

DOI：10.1002/mrc.3918

• C-13 NMR
• deuterium/hydrogen-induced effects
• alpha-D-glucose pentaacetate
• molecular modeling
• chemical shift calculations
• GIAO method

1,2,3,4,6-Penta-O-acetyl-alpha-D-glucopyranose and the corresponding [1-H-2], [2-H-2], [3-H-2], [4-H-2], [5-H-2], and [6,6-H-2(2)]-labeled compounds were prepared for measuring deuterium/hydrogen-induced effects on C-13 chemical shift (n)Delta ( 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 C-13 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)Delta DHIECS.

• 出版日期2013-3