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Paper | Special issue | Vol 37, No. 3, 1994, pp.1503-1510
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S63
Transmission of Electronic Effects through the Vinyl Group. Reactivities of the (E)-α-4-Substituted Phenyl-β-pyridineacrylic Acids

Milica Misic-Vukovic,* Sasa Drmanic, and Bratislav Jovanovic

*Facluty of Technology and Metallurgy, University of Belgrade, 11000 Belgrade, Yugoslavia

Abstract

The reactivities of a series of 18 (E)-α-4-substituted phenyl-β-(3N and 4N)pyridineaclylic acids, with a wide range of substituent effects, were investigated in their reaction with diazodiphenylmethane, in dimethylformamide at 30°C, by the known spectrophotometric method. The Hammett equation in its original form has been applied to the results, using the sum of substituent constants from the both aromatic nuclei, but the overall correlation was only fair. Better insight into the transmission of substituent effects was obtained using Taft’s Dual Substituent Parameter (DSP) method, where it was possible to distinguish the contributions from the inductive and resonance effects of the substituents.