Substituent effect on IR, 1H and 13C NMR spectral data in n-(substituted phenyl)-2-cyanoacetamides: A correlation study | Zendy

Аleksandar Marinković | Zendy; Dominik Brkić | Zendy; Jéléna Martinovic | Zendy; Dušan Mijin | Zendy; Miloš Milčić | Zendy; Slobodan Petrović | Zendy

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Substituent effect on IR, 1H and 13C NMR spectral data in n-(substituted phenyl)-2-cyanoacetamides: A correlation study

Author(s) -

Аleksandar Marinković,

Dominik Brkić,

Jéléna Martinovic,

Dušan Mijin,

Miloš Milčić,

Slobodan Petrović

Publication year - 2012

Publication title -

chemical industry and chemical engineering quarterly

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.189

H-Index - 26

eISSN - 2217-7434

pISSN - 1451-9372

DOI - 10.2298/ciceq120109044m

Subject(s) - substituent , chemistry , taft equation , carbon 13 nmr , delocalized electron , chemical shift , resonance (particle physics) , electrophile , proton nmr , electronic effect , computational chemistry , hammett equation , stereochemistry , organic chemistry , reaction rate constant , kinetics , physics , particle physics , quantum mechanics , steric effects , catalysis

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 (π-delocalization) within the π1-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

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