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

  • James E. Johnson
  • Diana C. Canseco
  • Debra D. Dolliver
  • Jeffrey E. Rowe
  • Frank R. Fronczek
Article

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).

KEY WORDS:

Crystal structure Enamine N-methoxyenamine N-methoxyoxime. 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • James E. Johnson
    • 1
  • Diana C. Canseco
    • 1
  • Debra D. Dolliver
    • 2
  • Jeffrey E. Rowe
    • 3
  • Frank R. Fronczek
    • 4
  1. 1.Department of Chemistry and PhysicsTexas Woman's UniversityDentonUSA
  2. 2.Department of Chemistry and PhysicsSoutheastern Louisiana UniversityHammondUSA
  3. 3.Department of ChemistryLa Trobe UniversityVic.Australia
  4. 4.Department of ChemistryLouisiana State UniversityBaton RougeUSA

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