TY - JOUR
T1 - Deuterium-induced isotope effects on the 13C chemical shifts of α- D -glucose pentaacetate
AU - Pérez-Hernández, Nury
AU - Álvarez-Cisneros, Celina
AU - Cerda-García-Rojas, Carlos M.
AU - Morales-Ríos, Martha S.
AU - Joseph-Nathan, Pedro
PY - 2013/3
Y1 - 2013/3
N2 - 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.
AB - 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.
KW - GIAO method
KW - chemical shift calculations
KW - deuterium/hydrogen-induced effects
KW - molecular modeling
KW - α- d -glucose pentaacetate
UR - http://www.scopus.com/inward/record.url?scp=84873731385&partnerID=8YFLogxK
U2 - 10.1002/mrc.3918
DO - 10.1002/mrc.3918
M3 - Artículo
C2 - 23315885
SN - 0749-1581
VL - 51
SP - 136
EP - 142
JO - Magnetic Resonance in Chemistry
JF - Magnetic Resonance in Chemistry
IS - 3
ER -