Abstract
The principles of linear free energy relationships were applied to the 1 H nmr and 13 C nmr chemical shifts induced by substituents in three isomeric trans-pyridineacrylic and substituted trans-cinnamic acids. The data for the carboxy proton chemical shift correlated well with the simple Hammett equation. Taft's dual substituent parameter equation was used for the interpretation of the balance of the inductive and resonance effects through the ethylenic bond for the C α and C β 13 C nmr shift. Using the nuclear Overhauser method, the conformation of the carboxylic group in 2-pyridineacrylic acid was determined, and its unexpected behaviour in both 1 H nmr chemical shifts;and in the previously studied reaction with diazodiphenylmethane was interpreted by the increased electron density in the π-electronic system favoured by the orbital symmetry of the part of the acid molecule
Published Version
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