New unsymmetrical difluoroaromatic compounds and estimation of their reactivities in nucleophilic substitution |
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Authors: | Keshtov M L Rusanov A L Keshtova S V Petrovskii P V Shchegolikhin A A |
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Institution: | (1) Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(2) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899 Moscow, Russian Federation;(3) Russian Academy of Sciences, N. M. Emanuel" Institute of Biochemical Physics, 4 ul. Kosygina, 119991 Moscow, Russian Federation |
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Abstract: | A series of previously unknown unsymmetrical difluoroaromatic compounds, viz., p-fluorobenzoylphenyl(p-fluorophenyl)-substituted imidazoles, pyrazines, and quinoxalines, were synthesized according to multistep procedures with the use of chloral as the key compound. The reactivities of the resulting difluoroaromatic compounds were estimated based on 19F and 13C NMR spectral data and the results of quantum-chemical calculations. The calculated charge densities on the Cipso atoms correlate linearly with the experimental chemical shifts in the 19F and 13C NMR spectra. Difluoroaromatic compounds, which are characterized by F > –110 and C > 163 and by the charge density on the Cipso atom higher than 0.08 e, are sufficiently activated to be used for the preparation of high-molecular-weight polyethers. |
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Keywords: | difluoroaromatic compounds quinoxalines pyrazines imidazoles reactivity 13C and 19F NMR spectroscopy charge density correlation |
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