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

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 structure Enamine N-methoxyenamine N-methoxyoxime. 


  1. 1.
    Lei, Y.X.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2001, 66, 8379–8394.CrossRefGoogle Scholar
  2. 2.
    Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405–10417.CrossRefGoogle Scholar
  3. 3.
    Neuvonen, K.; Zewi, C.; Lonnberg, H. Acta Chemica Scandinavica 1996, 50, 1137–1142.CrossRefGoogle Scholar
  4. 4.
    Al-Omari, H.S.M.; Zeitschrift furNaturforschung A, J. Phys. Sci. 2004, 59, 382–388.Google Scholar
  5. 5.
    Rowe, J.E.; Lee, K.; Dolliver, D.D.; Johnson, J.E. Aust. J. Chem. 1999, 52, 807–811.CrossRefGoogle Scholar
  6. 6.
    Johnson, J.E.; Dolliver, D.D.; Yu, L.; Canseco, D.C.; McAllister, M.A.; Rowe, J.E. J. Org. Chem. 2004, 69, 2741–2749.Google Scholar
  7. 7.
    Johnson, J.E.; Canseco, D.C.; Dolliver, D.D.; Rowe, J.E., unpublished work.Google Scholar
  8. 8.
    Baba, H.; Hori, I.; Hayashi, T.; Midorikawa, H. Bull. Chem. Soc. Japan, 1969, 42, 1653–1659.CrossRefGoogle Scholar
  9. 9.
    Huang, Z.-T.; Wang, M.-X. In The Chemistry of Enamines, Part 2; Rappoport, Z., Eds.; John Wiley and Sons, Ltd: New York, Chapter 16, 1994.Google Scholar
  10. 10.
    Arte, E.; Declerq, J.P.; Germain, G.; Van Meersche, M. Bull. Soc. Chem. Belg. 1978, 87, 573.Google Scholar
  11. 11.
    Newkome, G.R.; Baker, G.R. Organic Preparations and Procedures Int. 1986, 18, 117–144.CrossRefGoogle Scholar
  12. 12.
    Skarzewski, J. Tetrahedron 1989, 45, 4593–4598.CrossRefGoogle Scholar
  13. 13.
    Jones, J.R. The Ionisation of Carbon Acids, Academic Press: New York, 1973.Google Scholar
  14. 14.
    Orpen, A.G.; Brammer, L.; Kennard, O.; Watson, D.G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.Google Scholar
  15. 15.
    BIDICS, Institute for Material Research ; Hamiltion: Canada, 1969–1981.Google Scholar

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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