Chemical shifts calculations on aromatic systems: a comparison of models and basis sets

Abstract GIAO and CSGT models at Hartree–Fock and DFT/B3LYP levels of theory using different basis sets were employed for calculations of 1 H and 13 C NMR chemical shifts for para -X-substituted (X = H, CH 3 O and NO 2 ) aromatic carbonyl compounds. For these compounds the best choice to evaluate theoretical chemical shifts is B3LYP/cc-pVDZ using CSGT model.

[1]  Giuseppe Bifulco,et al.  Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. , 2002, Chemistry.

[2]  Trygve Helgaker,et al.  Ab Initio Methods for the Calculation of NMR Shielding and Indirect Spin-Spin Coupling Constants , 1999 .

[3]  P. Rossi,et al.  Calculation of 13C chemical shifts in rna nucleosides: structure-13C chemical shift relationships. , 2001, Journal of magnetic resonance.

[4]  V. Galasso.  On the n(N)/n(O) interaction in adamantane cages , 2000 .

[5]  T. H. Dunning.  Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen , 1989 .

[6]  Todd A. Keith,et al.  Calculation of magnetic response properties using atoms in molecules , 1992 .

[7]  E. Breitmaier,et al.  [Carbon 13 NMR spectroscopy]. , 1976, Pharmazie in unserer Zeit.

[8]  Thomas Gregor,et al.  A comparison of methods for the calculation of NMR chemical shifts , 1999 .

[9]  Todd A. Keith,et al.  Calculation of magnetic response properties using a continuous set of gauge transformations , 1993 .

[10]  Thom H. Dunning,et al.  Gaussian basis sets for use in correlated molecular calculations. V. Core-valence basis sets for boron through neon , 1995 .

[11]  Jacopo Tomasi,et al.  Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes , 1982 .

[12]  F. Jensen.  Introduction to Computational Chemistry , 1998 .

[13]  T. Keith,et al.  A comparison of models for calculating nuclear magnetic resonance shielding tensors , 1996 .

[14]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[15]  J. Tomasi,et al.  Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects , 1981 .

[16]  Giuseppe Bifulco,et al.  Determination of the relative stereochemistry of flexible organic compounds by Ab initio methods: conformational analysis and Boltzmann-averaged GIAO 13C NMR chemical shifts. , 2002, Chemistry.

[17]  J. Elguero,et al.  Synthesis, experimental and theoretical NMR study of 2′-hydroxychalcones bearing a nitro substituent on their B ring , 2004 .

[18]  B. Kovač,et al.  Structural and spectroscopic characterization of oxo-sparteines , 2004 .

[19]  L. Goodman,et al.  The Pharmacological Basis of Therapeutics , 1941 .

[20]  Raymond J. Abraham,et al.  Introduction to NMR Spectroscopy , 1988 .