Conclusions
From13C,15N,17O,19F,29Si,31P,73Ge,77Se,119Sn, and125Te NMR data, it follows that complete replacement of phenyl hydrogen atoms by fluorine in compounds C6H5X leads to a systematic increase in shielding of nuclei in the ring carbon atom bonded to the X group and in shielding of the nucleus of the α-atom of X, along with deshielding of the nuclei of the Β- and γ-atoms of X. The effect evidently has a long-range character and can be described by the extended theory of Dewar and Kelemen.
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Literature cited
The Sadtler Standard Spectra: Carbon-13 NMR Spectra, Sadtler Research Laboratories, Philadelphia, Vol. 3, No. 425 C (1976); Vol. 43, No. 8463C (1980); Vol. 63, No. 12476C (1982).
J. M. Briggs and E. W. Randal, J. Chem. Soc., Perkin Trans., 2, 1789 (1973).
A. I. Rezvukhin, G. G. Furin, G. A. Kalabin, et al., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Issue 5, No. 9, (1982).
M. J. S. Dewar and J. Kelemen, J. Chem. Phys.,49, 499 (1968).
A. V. Zibarev, G. N. Dolenko, S. A. Krupoder, et al., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Issue 2, No. 4, 73 (1980).
D. M. Kanjia, J. Mason, I. A. Stenhouse, et al., J. Chem. Soc., Perkin Trans.,2, 975 (1981).
A. I. Rezvukhin, G. G. Furin, and G. G. Yakobson, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2512 (1981).
G. G. Furin, A. I. Rezvukhin, M. A. Fedotov, and G. G. Yakobson, J. Fluorine Chem.,22, 231 (1983).
A. V. Zibarev, G. G. Furin, I. K. Korobeinicheva, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2259 (1983).
G. G. Furin, M. A. Fedotov, G. G. Yakobson, and A. V. Zibarev, J. Fluorine Chem.,28, 273 (1985).
J. Mason, Org. Magn. Reson.,10, 188 (1977).
J. Mason, J. Chem. Soc., Faraday Trans. 2,73, 1464 (1977).
A. A. Bakke, H. W. Chen, and W. L. Jolly, J. Electron Spectrosc. Relat. Phenom.,20, 333 (1980).
B. C. Trudell and S. J. W. Prise, Can. J. Chem.,56, 538 (1978).
G. G. Furin, A. V. Zibarev, L. N. Mazalov, and V. D. Yumatov, Electronic Structure of Organic Fluorine Compounds [in Russian], Nauka, Novosibirsk (1988).
J. Mason, J. Chem. Soc., Faraday Trans. 2,78, 1539 (1982).
G. N. Dolenko, A. V. Zibarev, S. A. Krupoder, and G. G. Furin, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Issue 2, No. 4, 81 (1980).
D. H. Evans, D. P. M. Mingos, J. Mason, and A. Richards, J. Organomet. Chem.,249, 293 (1983); K. von Werner and B. Wrackmeyer, J. Fluorine Chem.,31, 183 (1986); B. Wrackmeyer, K. von Werner, and F. Wehowsky, J. Fluorine Chem.,35, 359 (1987).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 829–832, April, 1989.
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Zibarev, A.V., Fedotov, M.A. & Fürin, G.G. Effect of fluorine replacement of hydrogen atoms in aromatic compounds on magnetic shielding of nuclei of heavy atoms at a distance from position of substitution. Russ Chem Bull 38, 744–747 (1989). https://doi.org/10.1007/BF00953284
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DOI: https://doi.org/10.1007/BF00953284