ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis, optical, and spectroscopic characterisation of substituted 3-phenyl-2-arylacrylonitriles

M. Judith Percino, Víctor M. Chapela, Enrique Pérez-Gutiérrez, Margarita Cerón, and Guillermo Soriano

Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 194, 22 Sur y San Claudio, C.P. 72570 Puebla, México

E-mail: jpercino@siu.buap.mx

Abstract: The Knoevenagel condensation between aldehydes and substrates with active methylene groups was applied to synthesise a series of 3-(4-substituted phenyl)-2-arylacrylonitriles (aryl = phenyl or pyridyl). Chloro-, fluoro-, or dimethylamino-substituted aryls and a cyano group attached to the double bond of acrylonitrile were studied. Previous studies showed that the condensation products were E isomers. The compounds synthesised were: 3-(4-chlorophenyl)-2-phenylacrylonitrile, 3-(4-chlorophenyl)-2-(pyridin-2-yl)acrylonitrile, 3-(4-chlorophenyl)-2-(pyridin-3-yl)acrylonitrile, 3-(4-chlorophenyl)-2-(pyridin-4-yl)acrylonitrile, 3-(4-fluorophenyl)-2-phenylacrylonitrile, 3-(4-fluorophenyl)-2-(pyridin-2-yl)acrylonitrile, 3-(4-fluorophenyl)-2-(pyridin-3-yl)acrylonitrile, 3-(4-fluorophenyl)-2-(pyridin-4-yl)acrylonitrile, 3-(4-dimethylaminophenyl)-2-phenylacrylonitrile, 3-(4-dimethylaminophenyl)-2-(pyridin-2-yl)acrylonitrile, 3-(4-dimethylaminophenyl)-2-(pyridin-3-yl)acrylonitrile, and 3-(4-dimethylaminophenyl)-2-(pyridin-4-yl)acrylonitrile. Structures were confirmed by IR, MS, and NMR spectral data. Molar absorption coefficient, absorbance, and fluorescence emission spectra were compared in order to evaluate the effects of substituents on phenyl and the position of nitrogen in pyridine moiety on the electronic properties of acrylonitrile derivatives prepared.

Keywords: solvent-free synthesis – Knoevenagel condensation – propenenitrile – 4-dimethylaminophenyl derivatives – phenylpyridylacrylonitriles

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0075-x

Chemical Papers 65 (1) 42–51 (2011)