Collect. Czech. Chem. Commun. 1979, 44, 1423-1433

Electronic structure and properties of alkoxymethylenemalonic acid derivatives

Dušan Ilavskýa, Jiří Krechlb, Petr Trškab and Josef Kuthanb

a Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava
b Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Six compounds RO(H)C=C(X)CN with R = CH3 or C2H5 and X = CO2CH3, CO2C2H5 or CN are characterized by some spectral data (IR, UV, 1H NMR - solvent effect). The PMR spectra did not confirm the presence of two geometrical isomers. Employing the quantum chemical calculations of the substance with R = CH3 and X = CO2CH3 based on EHT, PPP, HMO and CNDO/2, the geometrical isomerism is discussed in relation to the experimental dipole moments. The HMO indices of chemical reactivity agree with our present synthetic insight into nucleophilic substitution of the derivatives under study.