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N-substituted amides of 2-cyanopenta-2E,4-dienoic acid
Authors:I R Gol'ding  P V Petrovskii  O Ya Borbulevych  O V Shishkin  W Gruber  Yu G Gololobov  A N Shchegolikhin
Institution:(1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation;(2) Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001 Khar'kov, Ukraine;(3) Henkel KGaA, 67 Henkelstrasse, D-40191 Dusseldorf, Germany;(4) N. M. Emanuel' Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 117977 Moscow, Russian Federation
Abstract:N-Substituted amides of 2-cyanopenta-2E,4-dienoic acid were synthesized by condensation ofN-substituted cyanoacetamides with acrolein in a dioxane-DMSO solution in the presence of Zn(OAc)2·2H2O as a condensing agent. X-ray diffraction study of 3-methylanilide of 2-cyanopenta-2E,4-dienoic acid (2d) demonstrated that the crystal structure of this compound is similar to that of 2-cyanopenta-2E,4-dienoic acid studied previously. However, the presence of themeta-tolyl substituent in molecule2d apparently results in the fact that the β-structure, which is typical of 2-cyanopenta-2E,4-dienoic acid, does not exist in the crystalline phase of2d. Henkel Kommanditgesellschaft auf aktien, Deutschland, D-40191 Dusseldorf, Henkelstrasse, 67. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 933–937, May, 1999.
Keywords:N-substituted cyanoacetamides            N-substituted amides of 2-cyanopenta-2E  4-dienoic acid  X-ray diffraction study  molecular structure  crystal structure  IR spectra  Raman spectra  hydrogen bonds
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