1-Fluoroindan-1-carboxyic acid (FICA) derivatives containing a monosubstituted benzene ring were synthesized as their methyl esters and their potential as chiral derivatizing agents was assessed by both 19F and 1H NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2–2 fold increase in 19F values when compared with that of FICA. This increase was investigated using a correlation model for 19F NMR and by the order of the stability of the synperiplanar and antiperiplanar conformers of the (R,S) and (S,S) diastereomers from the Gibbs's free energy at 298.15 K.
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