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Michael addition of phenylacetonitrile to the acrylonitrile group leading to diphenylpentanedinitrile. Structural data and theoretical calculations

M. Judith Percino, Margarita Cerón, Maria Eugenia Castro, Guillermo Soriano-Moro, Victor M. Chapela, and Francisco J. Meléndez

Laboratorio de Polímeros, Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edificio 103 H, 22 Sur y San Claudio, Ciudad Universitaria, Puebla, 72570, México



Abstract: Knoevenagel condensation of phenylacetonitrile with 4-diphenylaminophenylacetonitrile in the presence of piperidine was carried out to obtain a novel conjugated compound. In addition to the expected compound 2-(phenyl)-3-(4-diphenylaminophenyl)acrylonitrile (I), the 3-((4-diphenylamino)phenyl)-2,4-diphenylpentanedinitrile (II) was also obtained with a good yield. Compound II was obtained as a result of the Michael addition of phenylacetonitrile with 2-(phenyl)-3-(4-diphenylaminophenyl)acrylonitrile (I). Conversely, when the same reaction was performed in the presence of KOH as catalyst, only the α,β-unsaturated nitrile (I) was afforded with a 92 % yield. The structures were confirmed with IR, EI-MS and NMR spectroscopy. Single crystals I and II were formed and their structures were determined by X-ray single-crystal diffraction analysis. Crystal I belongs to the monoclinic system with space group P21/n having unit cell parameters of a = 16.8589(5) Å, b = 6.68223(17) Å, c = 19.8289(7) Å, β = 111.133(4)○ and Z = 4. Crystal II belongs to the same monoclinic system with space group P21/c, having unit cell parameters of a = 10.8597(4) Å, b = 24.7533(10) Å, c = 9.7832(4) Å, β = 91.297(3)○ and Z = 4. In addition to the structural data analysis, some theoretical calculations that reveal the nature of relevant structure-property relationships are also reported.

Keywords: phenylacetonitrile – α,β-unsaturated nitrile – N-diphenylaminophenyl derivative – cyanosubstituted compound – Michael addition – crystal structure

Full paper is available at

DOI: 10.2478/s11696-013-0503-9


Chemical Papers 68 (5) 668–680 (2014)

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