Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids
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The C-13 NMR spectra of para-substituted alpha-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d(6)). The effect of substituents in both the alpha-phenyl and beta-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to C-13 NMR chemical shifts of the C-alpha and C-beta of the ethylenic bond and the carboxylic group carbon. Dissection of the alpha-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the pi-electronic system.
Keywords:NMR spectroscopy / spectra-structure correlation / para-substituted alpha-phenyl-pyridylacrylic acids
Source:Journal of Molecular Structure, 1997, 410, 39-41
- Elsevier, Amsterdam