Michael addition of phenylacetonitrile to the acrylonitrile group leading to diphenylpentanedinitrile. Structural data and theoretical calculations
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M. Percino
,
Margarita Cerón
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.
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© 2013 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- A spectrophotometric method for plant pigments determination and herbs classification
- Catalysis and reaction mechanisms of N-formylation of amines using Fe(III)-exchanged sepiolite
- Effect of support on activity of palladium catalysts in nitrobenzene hydrogenation
- Biphasic recognition chiral extraction — novel way of separating pantoprazole enantiomers
- Effect of the preparation route on the structure and microstructure of LaCoO3
- Synthesis, characterisation, and antioxidant study of Cr(III)-rutin complex
- Mercury(II) complexes of new bidentate phosphorus ylides: synthesis, spectra and crystal structures
- Synthesis and properties of CaAl-layered double hydroxides of hydrocalumite-type
- MgZnAl hydrotalcite-like compounds preparation by a green method: effect of zinc content
- Carbon nanotube-layered double hydroxide nanocomposites
- Synthesis of palladium-bidentate complex and its application in Sonogashira and Suzuki coupling reactions
- Reduction of nitroblue tetrazolium to formazan by folic acid
- Michael addition of phenylacetonitrile to the acrylonitrile group leading to diphenylpentanedinitrile. Structural data and theoretical calculations
- Efficient hydrolysis of glucose-1-phosphate catalyzed by metallomicelles with histidine residue
- Synthesis of [Re2Cl4(O)2(µ-O)(3,5-lut)4] and investigation of its structure via X-ray and spectroscopic measurements and DFT calculations
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