GIAO-DFT prediction of accurate NMR parameters in selected glucose derivatives

Abstract

Multinuclear magnetic resonance isotropic nuclear shieldings and their principal components for α‐ and β‐glucose and several related compounds were calculated at the DFT/6–31+G* level of theory using the B3PW91 density functional. The absolute values were converted to chemical shifts and compared with experiment. A good performance of the DFT method in the prediction of the GIAO NMR parameters for simple sugars was observed. The corresponding RHF results yielded significantly lower agreement with available experimental data. Copyright © 1999 John Wiley & Sons, Ltd.

Infrared, Raman and NMR spectra, conformational stability, normal coordinate analysis and B3LYP calculations of 5-amino-4-cyano-3-(methylthio)-1H-pyrazole-1-carbothioamide

“…Recently, DFT NMR calculations using Gauge-Invariant Atomic Orbitals (GIAO) model have became popular [28] and have been shown to successfully predict accurate chemical shifts (d, ppm) for small isolated molecules [22,[29][30][31][32]. While some studies seem to favor DFT predictions over the RHF method [31,32] the accuracy of NMR theoretical predictions most strongly depends on the implemented basis set and the optimized structural parameters.…”

“…While some studies seem to favor DFT predictions over the RHF method [31,32] the accuracy of NMR theoretical predictions most strongly depends on the implemented basis set and the optimized structural parameters. Here the simulated spectra where calculated using the B3LYP/6-31G(d) structural parameters for conformer 1.…”

“…11.008 size molecules up to 26 atoms [25][26][27]. In addition GIAO NMR DFT-B3LYP calculations have become popular aids to the interpretation of 1 H and 13 C chemical shifts [28][29][30][31][32][33][34][35][36]. Therefore, a thorough Raman, IR and NMR spectroscopic investigation is reported here complemented by B3LYP theoretical predictions [20][21][22][23][24] with bases sets up to 6-31++G(d,p) to provide novel insight on vibrational assignments and conformational stability of AMPC.…”

Conformational Analysis of Gentiobiose Using Genetic Algorithm Search and GIAO DFT Calculations with13C CPMAS NMR as a Verification Method

“…Similar procedures were used by Kupka et al, [31] where GIAO DFT calculations of glucose derivatives were performed on MM+ optimized structures with satisfactory accuracy of predicted NMR parameters. Forsyth and Sebaga [32] compared the calculated chemical shifts of many different compounds using both ab initio and molecular mechanics (MM3)-optimized structures as inputs for GIAO DFT calculations followed by empirical scaling of thus obtained shielding constants.…”

Quantum chemistry studies on the Ru–M interactions and the 31P NMR in [Ru(CO)3(Ph2Ppy)2(MCl2)] (M=Zn, Cd, Hg)

“…The application of density functional theory (DFT) has been especially useful for large organic molecules or molecules with transition metal atoms [30][31][32][33]. Among methods employed to calculate the NMR parameters such as CSGT, IGLO, GIAO and IGAIM, the GIAO method shows the best basis-set convergence and is employed by most quantum chemistry programs capable of computing nuclear shielding [30,34]. A number of applications have shown that the GIAO-DFT method is capable of reproducing experimental values for chemical shifts of transition metal complexes.…”