Abstract
Using the methods of IR spectroscopy, 13C NMR spectroscopy, and quantum‐mechanical methods (semiempirical AM1 and PM3 methods and the method of the density functional theory), we have investigated the tautomerism and spectral properties of 2‐anilinomethylenecyclopentane‐1,3‐dione. It is shown that this compound in crystals and solutions in CCl4 and CHCl3 exists in the form of a tautomer with an exocyclic arrangement of the C=C bond and a NH group participating in the formation of an intramolecular hydrogen bond with a carbonyl group of the carbocycle.
Similar content being viewed by others
REFERENCES
S. Forsen, F. Merenyi, and M. Nilson, Acta Chem. Scand., 18, 1208–1221 (1964).
D. B. Rubinov, L. L. Rubinova, and A. A. Akhrem, Chem. Rev., 99, 1047–1065 (1999).
É Yu. Gudrinietse (ed.), The Structure and Tautomeric Transformations of ????????-Dicarbonyl Compounds [in Russian], Riga (1977).
V. Z. Kurbako, V. V. Gromak, V. G. Avakyan, and S. V. Rykov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 40, 1299–1304 (1991).
V. G. Avakyan, V. V. Gromak, and A. E. Yatsenko, Rus. Chem. Bull., 43, 50–54 (1994).
V. G. Avakyan, V. V. Gromak, A. E. Yatsenko, A. N. Shchegolikhin, and N. A. Kubasova, Russ. Chem. Bull., 44, 1005–1010 (1995).
V. V. Gromak, V. G. Avakyan, and O. F. Lakhvich, Zh. Prikl. Spektrosk., 67, 154–161 (2000).
E. V. Borisov, T. S. Khlebnikova, D. V. Rubinov, and F. A. Lakhvich, J. Org. Chem. USSR, 28, 1304–1305 (1992).
H. Günther, NMR Spectroscopy. An Introduction, Wiley, New York (1980).
K. Saito and T. Yamaguchi, J. Chem. Soc. Perkin II, No. 12, 1605–1609 (1979).
E. Liepins, M. V. Petrova, E. Gudriniece, J. Paulins, and S. L. Kuznetsov, Magn. Reson. Chem., 27, 907–915 (1989).
S. Forsen, F. Merenyi, and M. Nilson, Acta Chem. Scand., 21, 620–624 (1967).
A. V. Iohansen and M. Sh. Rosenberg, Zh. Prikl. Spektrosk., 9, 1027–1030 (1968).
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. Stewart, J. Am. Chem. Soc., 107, 3902–3909 (1985).
J. J. Stewart, J. Comput. Chem., 10, 209–213 (1989).
J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 77, 3865–3868 (1996).
D. N. Laikov, J. Chem. Phys., 281, 151–156 (1997).
D. N. Laikov, Development of an Economic Approach to the Calculation of Molecules by the Method of Density Functional Theory and Its Application to the Solution of Complex Chemical Problems, Dissertation for the degree of Candidate of Physical and Mathematical Sciences, Moscow (2000).
C. Adamo and V. Barone, J. Chem. Phys., 110, 6158–6170 (1999).
V. G. Dashevskii, Conformations of Organic Molecules [in Russian], Moscow (1974), pp. 35, 43.
V. G. Avakyan, V. V. Gromak, and V. Z. Kurbako, Bull. Acad. Sci. USSR, Div. Chem. Sci., 38, 2188–2192 (1989).
K. Nakanishi, Infrared Absorption Spectroscopy, Holden-Day Inc., San Francisco, and Nancodo Company Limited, Tokyo (1962).
M. Yu. Antipin, M. V. Petrova, Ya. Ya. Paulinsh, Yu. T. Struchkov and É. Yu. Gudrinietse, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 1, 102–107 (1989).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gromak, V.V., Avakyan, V.G. & Pashkovskii, F.S. Tautomerism and Spectral Properties of 2‐Anilinomethylenecyclopentane‐1,3‐Dione According to the Data of Quantum‐Mechanical Calculations, IR Spectroscopy, and Secondary Isotopic Effects in the 13C NMR Spectra. Journal of Applied Spectroscopy 68, 259–266 (2001). https://doi.org/10.1023/A:1019216203002
Issue Date:
DOI: https://doi.org/10.1023/A:1019216203002