Abstract
2-Benzylidene-4-aza-1,3-indanediones have been synthesized and their structures have been investigated by NMR spectroscopy and quantum chemistry in the AM1 approximation. It was established that rotation about the exocyclic C(2)=C(10) formal double bond occurs in chloroform solutions of these compounds. The energy characteristics of this process have been determined experimentally and estimated theoretically.
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S. Jursenas, V. Gulbinas, A. Gruodis, G. Kodis, V. Kovalevskij, and L. Valkunas, Phys. Chem. Chem. Phys., 1, 1715 (1999).
J. Gulbis and V. Kampars, Scientific Proceedings of Riga Technical University, Material Science and Applied Chemistry, 11, 11 (2005).
V. Kampars, M. Utinans, P. Pastors, E. Kalnina, and V. Grazulevicus, Scientific Proceedings of Riga Technical University, Material Science and Applied Chemistry, 9, 148 (2004).
O. Neilands, Latv. J. Physics Techn. Sci., No. 4, 28 (1998).
B. Benassi, C. Bertarini, E. Kleinpeter, and F. Taddei, J. Mol. Struct. (Theochem), 498, 217 (2000).
R. R. Pappalardo, E. S. Marcos, M. F. Ruiz-Lopez, D. Rinaldi, and J.-L. Rivail, J. Am. Chem. Soc., 115, 3722 (1993).
N. Z. Tugusheva, S. Yu. Ryabova, N. P. Solov'eva, and V. G. Granik, Khim. Geterotsikl. Soedin., 781 (1994). [Chem. Heterocycl. Comp., 30, 683 (1994)].
M. Nogrady, Stereochemistry. Fundamental Concepts and Applications [Russian translation], Mir, Moscow (1984), p. 216.
J. Sandstrom, Dynamic NMR Spectroscopy, Acad. Press, New York (1982), p. 93.
M. Petrova, V. Negrebetsky, A. Rekis, A. Strakovs, J. Pauliņš, and E. Gudriniece, Latv. J. Chem., 474 (1993).
C. J. Pourchert and J. Behnke, The Aldrich Library of 13 C and 1 H FT NMR Spectra, Vol. 2 (1993).
J. L. Leroy, K. Snoussi, and M. Gueron, Magn. Res. Chem., 39, 171 (2001).
M. Sigalov, A. Vashchenko, and V. Khodorkovsky, J. Org. Chem., 70, 92 (2005).
J. J. P. Stewart, MOPAC, Version 6; QCPE N 455: Bloomington (1984).
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1024–1032, July, 2008.
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Petrova, M., Liepinsh, E., Pastors, P. et al. Synthesis of 2-(4′-R-benzylidene)-4-aza-1,3-indanediones and investigation of isomerization around the exocyclic double bond. Chem Heterocycl Comp 44, 820–827 (2008). https://doi.org/10.1007/s10593-008-0115-4
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DOI: https://doi.org/10.1007/s10593-008-0115-4