Collect. Czech. Chem. Commun. 1984, 49, 421-432

13C NMR and IR study of substitution effects and mass spectra of biphenyl analogues of α-cyanochalcones

Štefan Marchalín, Petr Trška and Josef Kuthan

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Thirteen biphenyl analogues of α-cyanochalcones IIa-IIm were prepared by condensation of p-phenylbenzoylacetonitrile (I) with p-substituted benzaldehydes. Their 13C NMR chemical shifts were measured and correlated with the Hammett parameters (σ, σ+) and the Swain-Lupton reactivity parameters. A consistent picture of the transmission of the substituent (electronic) effects through the carbon skeleton of the studied compounds was obtained. The relationship between the structure of synthetized α-cyanochalcones and their mass spectra is discussed.