Abstract
Ten mono-, di-, and trinitro derivatives of N-methyl-N-nitroaniline were synthesized and studied by spectral, electrooptical, and quantum-chemical methods. Three of these derivatives, N-methyl-N,2,3-trinitroaniline, N-methyl-N,2,5-trinitroaniline, N-methyl-N,3,5-trinitroaniline, were also examined by the X-ray diffraction method. The N-nitroamino group in their molecules is almost planar, the N7-N8 bond is shortened, and the N8 atom is characterized by a strong deficit of electron density. The dihedral angle between the planes of the N-nitroamino group and the benzene ring is 56°–92°, which makes conjugation between these fragments impossible. The N-nitroamino group in the examined compounds acts as a weak electron donor with respect to the nitro groups in the aromatic ring; the mechanism of this effect is inductive.
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Original Russian Text © V.V. Prezhdo, A.S. Bykova, O.V. Prezhdo, Z. Daszkiewicz, J.B. Kyziol. J. Zaleski, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 1, pp. 69–80.
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Prezhdo, V.V., Bykova, A.S., Prezhdo, O.V. et al. Synthesis, properties, and molecular structure of nitro-substituted N-methyl-N-nitroanilines. Russ J Gen Chem 76, 64–75 (2006). https://doi.org/10.1134/S1070363206010142
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DOI: https://doi.org/10.1134/S1070363206010142