Synthesis, characterization, and structural analysis of ethyl (2Z)-3-(4-chlorophenyl)-2-cyano-3-(methoxyamino)prop-2-enoate |
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| Authors: | James E Johnson Diana C Canseco Debra D Dolliver Jeffrey E Rowe Frank R Fronczek |
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| Institution: | (1) Department of Chemistry and Physics, Texas Woman's University, P.O. Box 425859-5859, Denton, Texas 76204-5859, USA;(2) Department of Chemistry and Physics, Southeastern Louisiana University, Hammond, Louisiana 70402, USA;(3) Department of Chemistry, La Trobe University, Vic., 3086, Australia;(4) Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA |
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| Abstract: | Ethyl (2Z)-3-(4-chlorophenyl)-2-cyano-3-(methoxyamino)prop-2-enoate was prepared by reacting the lithium salt of ethyl cyanoacetate with (Z)-O-methyl-4-chloroben-zohydroximoyl fluoride. This compound crystallizes in space group Pbca,with lattice constants a=7.5740(15) ?, b=11.337(2) ?, and c=30.424(5) ? at 110 K. Characterizations include spectrometric identifications employing IR, UV, and 1H and 13C NMR. The compound exists in the solid as the enamine tautomer, with the cyano group cis to the 4-chlorophenyl group (the Z configuration). The C=C and C–N bond distances are 1.3930(16) ? and 1.3278(16) ?, respectively. The N–H group forms a bifurcated hydrogen bond with acceptors C=O (intramolecular) and C≡N (intermolecular).Supplementary material CCDC-289444 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(0)1223-336033. |
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| Keywords: | Crystal structure Enamine N-methoxyenamine N-methoxyoxime |
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