Comparison of carbon-13 nuclear magnetic resonance methods for the analysis of multiple partially deuteriated products from catalytic reactions: heptan-1-ol and 2-methylpropanol

Abstract

Products from the hydrocarbonylation of hex-1-ene or prop-2-en-1-ol using H₂–CO or D₂–CO in EtOH or EtOD have been analysed using ¹³C NMR techniques. Where there are up to four isotopomers in the products, analysis of β-shifted resonances in the ¹³C-{¹H} NMR spectrum can give enough information for quantification of all isotopomers. Using prop-2-en-1-ol, D₂–CO and EtOH, the 2-methylpropanol produced is a mixture of 16 different isotopomers. These can be individually quantified by analysis of the ¹³C-{¹H, ²D} NMR spectrum. In particular, the resonance from the methyl C atom shows β and γ shifts, the latter being different for different types of γ-D atom. These analytical methods are shown to be superior to other possibilities including ¹H NMR and mass spectrometry.