Journal of Chemical Crystallography

, Volume 36, Issue 10, pp 667–672

Synthesis, characterization, and structural analysis of ethyl (2Z)-3-(4-chlorophenyl)-2-cyano-3-(methoxyamino)prop-2-enoate


    • Department of Chemistry and PhysicsTexas Woman's University
  • Diana C. Canseco
    • Department of Chemistry and PhysicsTexas Woman's University
  • Debra D. Dolliver
    • Department of Chemistry and PhysicsSoutheastern Louisiana University
  • Jeffrey E. Rowe
    • Department of ChemistryLa Trobe University
  • Frank R. Fronczek
    • Department of ChemistryLouisiana State University

DOI: 10.1007/s10870-006-9115-3

Cite this article as:
Johnson, J.E., Canseco, D.C., Dolliver, D.D. et al. J Chem Crystallogr (2006) 36: 667. doi:10.1007/s10870-006-9115-3

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) Å, b=11.337(2) Å, and c=30.424(5) Å 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) Å and 1.3278(16) Å, respectively. The N–H group forms a bifurcated hydrogen bond with acceptors C=O (intramolecular) and C≡N (intermolecular).


Crystal structureEnamineN-methoxyenamineN-methoxyoxime.

Copyright information

© Springer Science+Business Media, Inc. 2006