A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones

Abstract

Substituent effects on the IR stretching frequencies and 1H-NMR chemical shifts of the pyridone NH group in 4- and 6-disubstituted alkyl and aryl 3-cyano-2-pyridones were investigated. The bands most sensitive to substituent effects from the broad and multiple IR NH band for each compound were selected by a computer calculation. The selected values of the IR frequencies and the determined 1H-NMR chemical shifts were subjected to LFER analysis, by correlations with the Hamett σm/p and Swain–Lupton F and R substituent constants.

Keywords

• substituted 2-pyridones
• LFER analysis
• NH bond
• IR and 1H-NMR spectra