Fluorine‐induced shifts of neighbouring protons were studied by comparing the 1H NMR data of 20 fluorinated retinal isomers and their non‐fluorinated counterparts. Concurrent 19F NMR data of various isomers, analysed with respect to those of the all‐trans fluorinated isomers, showed an interactive effect between the γ‐protons and F. Successful application of the observed trends in 1H NMR and 19F NMR chemical shifts to retinylidene Schiff bases and protonated Schiff bases demonstrates their importance as practical aids in assigning configuration and predicting relative 1H NMR and 19F NMR resonances.
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Colmenares et al. (1992) studied this question.
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