Abstract
The crystal and molecular structure of the methyl ester ofα-cyanocinnamic acid [(E)-methyl-α-cyanocinnamate] has been determined from three-dimensional X-ray data. C11H9NO2 is monoclinic, space groupC2/c,Z=8,a=12.386(2),b=8.237(1),c=19.320(2) Å,β=98.49(5)°. The He(I) and He(II) photoelectron (PE) spectra of (E)-methyl-α-cyanocinnamate are presented and discussed in comparison with those of previously investigated molecules, within a comprehensive investigation of the electronic structure ofα,β-dehydroamino acid derivatives and related compounds.
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References
Ajò, D., Busetti, V., Ottenheijm, H. C. J., and Plate, R. (1984a)Acta Cryst. C 40, 324, and refs. therein.
Ajò, D., Casarin, M., Bertoncello, R., Busetti, V., Ottenheijm, H. C. J., and Plate, R. (1985)Tetrahedron 41, 5543.
Ajò, D., Casarin, M., Granozzi, G., Ottenheijm, H. C. J., and Plate, R. (1984b)Recueil des Travaux Chimiques des Pays-Bas 103, 365.
Ajò, D., Casarin, M., Granozzi, G., and Rizzardi, G. (1983)J. Mol. Struct. 101, 167.
Ajò, D., Granozzi, G., Tondello, E., and Del Pra, A. (1980)Biopolymers 19, 469.
Ajò, D., Granozzi, G., Tondello, E., Del Pra, A., and Zanotti, G. (1979)J. Chem. Soc. Perkin Trans. II, 927.
Avenoza, A., Cativiela, C., Mayoral, J. A., and Roy, M. A. (1989)Tetrahedron 45, 3923.
Bueno, M. P., Cativiela, C., Finol, C., Mayoral, J. A., and Jaime, C. (1987)Can. J. Chem. 65, 2182.
Busetti, V., Ajò, D., and De Zuane, F. (1988b)Zeitschrift Kristall. 184, 203, and refs. therein.
Busetti, V., Mayoral, J. A., Cativiela, C., Ajò, D. and Casarin, M. (1988a)J. Crystall. Spectrosc. Res. 18, 75, and refs. therein.
Busetti, V., Mayoral, J. A., Cativiela, C., Diaz de Villegas, M. D., and Ajò, D. (1989)Zeitschrift Kristall. 189, 65.
Hayashi, T. (1966)J. Org. Chem. 31, 3253.
Horikawa, H., Nishitani, T., Iwasaki, T., Mushika, Y., Inoue, I., and Miyoshi, M. (1980)Tetrahedron Lett. 21, 4101.
International Tables for X-ray Crystallography (1974) (Kynoch Press, Birmingham) (second edition).
Johnson, C. K. (1976)Ortep II. Report ORNL-5138. (Oak Ridge National Laboratory, Oak Ridge, Tenn.).
Kimura, K., Katsumata, S., Achiba, Y., Yamazaki, T., and Iwata, S. (1981)Handbook of Hel Photoelectron Spectra of Fundamental Organic Molecules (Japan Scientific Socieites Press, Tokyo; Halsted Press, New York).
Lapworth, A., and Baker, W. (1947)Organic Synthesis Col., Vol. I, p. 181–182. (Wiley, New York).
Main, P., Hull, S. E., Lessinger, L., Germain, G., Declercq, J.-P., and Woolfson, M. M.,“MULTAN78.” A System of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data. (University of York, England, Louvain, Belgium).
Mayoral, J. A., Cativiela, C., Lopez, M. P., Ajò, D., and De Zuane, F. (1989)J. Cryst. Spectr. Res.,19, 993.
Noda, K., Shimohigashi, Y., and Izumiya, N. (1983) in ThePeptides, Analysis, Synthesis, Biology Vol. V, E. Gross and J. Meienhofer, eds., Academic Press, New York, pp. 285–289.
Rich, D. H., and Bhatnagar, P. K. (1978)J. Am. Chem. Soc. 100, 2218.
Schmidt, U., Häusler, J., Oehler, E., and Poisel, H. (1979) inProgress in the Chemistry of Natural Products Vol. 37, W. Herz, H. Grisebach, and G. W. Kirby, eds., Springer Verlag, New York, p. 251.
Sheldrick, G. M. (1976)SHELX. Program for Crystal Structure Determination, University of Cambridge.
Tager, H. S., and Christensen, H. N. (1972)J. Am. Chem. Soc. 94, 968.
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Busetti, V., Mayoral, J.A., Cativiela, C. et al. Structural investigation of compounds related to α,β-dehydroaminoacids: (E)-methyl-α-cyanocinnamate. Journal of Crystallographic and Spectroscopic Research 20, 545–550 (1990). https://doi.org/10.1007/BF01221895
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DOI: https://doi.org/10.1007/BF01221895