Deuterium‐induced isotope effects on the 13C chemical shifts of α‐d‐glucose pentaacetate |
| |
| Authors: | Nury Pérez‐Hernández Celina Álvarez‐Cisneros Carlos M Cerda‐García‐Rojas Martha S Morales‐Ríos Pedro Joseph‐Nathan |
| |
| Institution: | 1. Programa Institucional de Biomedicina Molecular, Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, , México, D. F., 07320 Mexico;2. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, , México, D. F., 07000 Mexico |
| |
| Abstract: | 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. Copyright © 2013 John Wiley & Sons, Ltd. |
| |
| Keywords: | 13C NMR deuterium/hydrogen‐induced effects α ‐d‐glucose pentaacetate molecular modeling chemical shift calculations GIAO method |
|
|
