Indirect nuclear spin-spin coupling constants and chemical shifts in norbornene- derivatives bearing boronic acid pinacol ester group

Abstract

We have simulated the nuclear magnetic resonance (NMR) parameters of ten norbornene-derivativesbearing a boronic acid pinacol ester group. In particular, we have calculated the 13C and 1H chemicalshifts and proton-proton indirect nuclear spin-spin coupling constants in order to confirm or revisethe assignment of the measured NMR parameters. The calculations were carried out at the level ofdensity functional theory with the B3LYP exchange-correlation functional and the cc-pVTZ-J basisset, which is specially optimized for the calculation of NMR coupling constants. We found, that withthis level of theory one obtains good agreement with most of the experimental assignations. Thisapproach could be a useful tool to help in assignment of both chemical shifts and spin-spin couplingsconstants for mixture of diastereomers.