Conclusions
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1.
It has been established by X-ray structural analysis that the highly polar form of 1-(4-nitrophenyl)-3,5,5-triphenylformazan has the structure of the E1,2, E2,3, E3,3-isomer.
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2.
The specificity of the electronic and spatial structure of this isomer (acceptor NO2 and donor PhN group linked by a fairly planar system of conjugation) permits its high dipole moment to be explained by intramolecular charge transfer.
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3.
Conjugation plays a fundamental role in the determination of the conformation of sterically hindered hydrazones.
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4.
The conformation of the diphenylamino group in compounds of various classes is due both to intramolecular factors and to the nature of the packing in the crystal.
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Translated from Izvestiya Akad'emii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1306–1313, 1982.
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Buzykin, B.I., Cherepinskii-Malov, V.D., Litvinov, I.A. et al. Crystal and molecular structure of 1-(4-nitrophenyl)-3,5,5-triphenylformazan. Russ Chem Bull 31, 1164–1170 (1982). https://doi.org/10.1007/BF00955970
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DOI: https://doi.org/10.1007/BF00955970