Spectral correlation, antimicrobial and insect antifeedant activities of some 1-naphthyl keto-oxiranes

• Main Author: G. Thirunarayanan
• Format: Article
• Language: English
• Published: Elsevier 2014-12-01
• Series: Journal of Saudi Chemical Society
• Subjects: 1-Naphthyl keto-oxiranes; Synthesis; IR and NMR spectra; Substituent effects; Antimicrobial and insect antifeedant activities
• Online Access: http://www.sciencedirect.com/science/article/pii/S1319610311001992

Thirteen optically active (αS,βR) 1-naphthyl keto-oxiranes (1-naphthyl-4-yl[3-(substituted phenyl)oxiran-2-yl]methanones) have been synthesised by phase transfer catalysed epoxidation of 1-naphthyl chalcones. The yields of oxiranes are more than 95%. The synthesized oxiranes have been characterized by IR, 1H, 13C and MS spectra. The spectral data are correlated with Hammett substituent constants and Swain–Lupton parameters. From the regression analysis the effect of substituent on the group frequencies has been predicted. The antimicrobial and insect antifeedant activities of all synthesised oxiranes have been evaluated.