Analysis of two-dimensional nuclear magnetic resonance spectra with relayed proton-proton-carbon magnetization transfer: a step toward automated structure elucidation

Procedures are described for automated anal. of two-dimensional NMR spectra correlating the chem. shifts of carbon-13 with the shifts of neighbor protons that are directly attached to the carbon-13 nuclei and with remote protons that have scalar couplings to the neighbor protons. The anal. yields connectivity matrixes with quality factors that provide a measure for the reliability of the evidence. The connectivity matrixes can be represented graphically either by drawing the paths of magnetization transfer onto the mol. formula or by indicating the connectivities in conventional shift correlation spectra. Applications are shown to 2-thiophenecarboxylic acid, to 1-hexanol, to 2,6-dimethylcyclohexanol, and to (1RS,2SR,4SR,5RS,6RS)-6-exo-(2-nitrophenylthio)spiro[bicyclo[2.2.2]octane-2,2'-oxirane]-5-endo-yl chloride. [on SciFinder (R)]