%0 Journal Article
%T Substituent effect on IR, 1H and 13C NMR spectral data in n-(substituted phenyl)-2-cyanoacetamides: A correlation study
%A Marinkovi£¿ Aleksandar D.
%A Brki£¿ Dominik
%A Martinovi£¿ Jelena S.
%A Mijin Du£¿an £¿.
%J Chemical Industry and Chemical Engineering Quarterly
%D 2013
%I Association of the Chemical Engineers
%R 10.2298/ciceq120109044m
%X Linear free energy relationships (LFER) were applied to the IR, 1H and 13C NMR spectral data of N-(substituted phenyl)-2-cyanoacetamides. A variety of substituents were employed for phenyl substitution and fairly good correlations were obtained using the simple Hammett and the Hammett-Taft dual substituent parameter equations. The correlation results of the substituent induced 13C NMR chemical shifts (SCS) of the C1, C=O and N-H atom indicated different sensitivity with respect to electronic substituent effects. A better correlation of the SCSC=O with a combination of electrophilic and nucleophilic substituent constants indicated a significant contribution of extended resonance interaction (¦Ğ-delocalization) within the ¦Ğ1-unit. The conformations of the investigated compounds were studied using the DFT B3LYP/6-311G method and, together with the results of 13C NMR and IR spectroscopic studies, a better insight into the influence of such a structure on the transmission of electronic substituent effects was obtained.
%K N-(substituted phenyl)-2-cyanoacetamides
%K LFER analysis
%K IR and NMR spectra
%K SCS shift
%K Hammett equation
%U http://www.doiserbia.nb.rs/img/doi/1451-9372/2013/1451-93721200044M.pdf