• michael addition of phenylacetonitrile to the acrylonitrile group leading to diphenylpentanedinitrile. structural data and theoretical calculations

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    • تاریخ ارائه: 1392/07/24
    • تاریخ انتشار در تی پی بین: 1392/07/24
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     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 ibelongs 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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