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Molecular complexes of 4-nitropyridine and 4-nitroquinoline N-oxides with boron trifluoride and hydrogen chloride as intermediates in SNAr reactions

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Abstract

Complexation of 4-nitropyridine N-oxides with ν- (BF3, HCl) and π-acceptors (tetracyanoethylene, chloranil, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 7,7,8,8-tetracyanoquinodimethane) activates the nitro group to nucleophilic replacement by chlorine. Adducts formed by 4-nitropyridine and 4-nitroquinoline N-oxides with boron trifluoride and hydrogen chloride were studied by IR spectroscopy. It was shown that these complexes belong to the n,ν type and that the donor-acceptor interaction therein involves the oxygen atom of the N-oxide group.

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References

  1. Andreev, V.P. and Ryzhakov, A.V., Khim. Geterotsikl. Soedin., 1999, p. 1443.

  2. Ryzhakov, A.V., Vapirov, V.V., and Rodina, L.L., Zh. Org. Khim., 1991, vol. 27, p. 955.

    CAS  Google Scholar 

  3. Ryzhakov, A.V. and Rodina, L.L., Zh. Org. Khim., 1994, vol. 30, p. 1417.

    CAS  Google Scholar 

  4. Andreev, V.P. and Nizhnik, Ya.P., Russ. J. Org. Chem., 2001, vol. 37, p. 141.

    Article  CAS  Google Scholar 

  5. Andreev, V.P., Ryzhakov, A.V., and Kalistratova, E.G. Khim. Geterotsikl. Soedin., 1996, p. 516.

  6. Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58, p. 380.

    Article  Google Scholar 

  7. Swift, J.A., Pivovar, A.M., Reynolds, A.M., and Ward, M.D., J. Am. Chem. Soc., 1998, vol. 120, p. 5887.

    Article  CAS  Google Scholar 

  8. Trotter, J., Acta Crystallogr., 1960, vol. 13, p. 95.

    Article  CAS  Google Scholar 

  9. Yatsenko, A.V., Paseshnichenko, K.A., Chernyshev, V.V., and Schenk, H., Acta Crystallogr., Sect. C, 2001, vol. 57, p. 397.

    Article  CAS  Google Scholar 

  10. Filippenko, O.S., Chuev, I.I., Leonova, L.S., Shilov, G.V., and Adoshin, S.M., Dokl. Ross. Akad. Nauk, 2001, vol. 376, p. 27.

    Google Scholar 

  11. Kovalevskii, A.Yu., Ponomarev, I.I., Antipin, M.Yu., Ermolenko, I.G., and Shishkin, O.V., Izv. Ross. Akad. Nauk, Ser. Khim., 2000, p. 68.

  12. Yutilov, Yu.M. and Svertilova, I.A., Khim. Geterotsikl. Soedin., 1994, p. 1071.

  13. Andreev, V.P., Nizhnik, Ya.P., Bezruchko, D.G., and Morozov, A.K., Russ. J. Gen. Chem., 2005, vol. 75, p. 1309.

    Article  CAS  Google Scholar 

  14. Baert, F., Schweiss, P., Heger, G., and More, M., J. Mol. Struct., 1988, vol. 178, p. 29.

    Article  CAS  Google Scholar 

  15. Li, S.-X., Wang, Z.-M., Chen, J.-Z., and Su, W.-Y., Chin. J. Struct. Chem., 1993, vol. 12, p. 35; Chem. Abstr., 1994, vol. 121, no. 25 450 b.

    CAS  Google Scholar 

  16. Peover, M.E., J. Chem. Soc., 1962, p. 4540.

  17. Ochiai, E., J. Org. Chem., 1953, vol. 18, p. 534.

    Article  CAS  Google Scholar 

  18. Talik, T. and Talik, Z., Roczn. Chem., 1962, vol. 36, p. 539.

    CAS  Google Scholar 

  19. Taylor, E.C. and Crovetti, A.J., J. Org. Chem., 1954, vol. 19, p. 1633.

    Article  CAS  Google Scholar 

  20. Suszko, J. and Szafran, M., Roczn. Chem., 1965, vol. 39, p. 709.

    CAS  Google Scholar 

  21. Kubota, T., J. Pharm. Soc. Jpn., 1954, vol. 74, p. 831.

    CAS  Google Scholar 

  22. Chmurzynski, L., Molecules, 1997, vol. 2, p. 169.

    Article  CAS  Google Scholar 

  23. Ponomarenko, S.P., Borovikov, Yu.Ya., Kukhar’, V.P., Makovetskii, V.P., and Borovikov, S.Yu., Russ. J. Gen. Chem., 1998, vol. 68, p. 1271.

    CAS  Google Scholar 

  24. Huyskens, P., Sobczyk, L., and Majerz, I., J. Mol. Struct., 2002, vol. 615, p. 61.

    Article  CAS  Google Scholar 

  25. Dega-Szafran, Z., Katrusiak, A., Szafran, M., and Tykarska, E., J. Mol. Struct., 1999, vol. 484, p. 49.

    Article  CAS  Google Scholar 

  26. Garvey, R.G., Nelson, J.N., and Ragsdale, R.O., Coord. Chem. Rev., 1968, vol. 3, p. 375.

    Article  CAS  Google Scholar 

  27. Dega-Szafran, Z., Grundwald-Wyspiańska, M., Kania, A., Kosturkiewicz, Z., Tykarska, E., and Szafran, M., J. Mol. Struct., 1995, vol. 356, p. 169.

    Article  CAS  Google Scholar 

  28. Hanuza, J., Mączka, M., Waskowska, A., Oganowski, W., Ban-Oganowska, H., Lutz, E.T.G., and van der Maas, J.H., J. Mol. Struct., 1998, vol. 450, p. 201.

    Article  CAS  Google Scholar 

  29. Kulevsky, N. and Sveum, L., J. Inorg. Nucl. Chem., 1965, vol. 27, p. 2111.

    Article  CAS  Google Scholar 

  30. Gates, P.N. and Mooney, E.F., J. Inorg. Nucl. Chem., 1968, vol. 30, p. 839.

    Article  CAS  Google Scholar 

  31. Andreev, V.P. and Ryzhakov, A.V., Khim. Geterotsikl. Soedin., 1994, p. 1087.

  32. Kida, S., Quagliano, J.V., Walmsley, J.A., and Tyree, S.Y., Spectrochim. Acta, 1963, vol. 19, p. 189.

    Article  CAS  Google Scholar 

  33. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 443.

    Google Scholar 

  34. Burg, A.B. and Bickerton, J.H., J. Am. Chem. Soc., 1945, vol. 67, p. 2261.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Petrozavodsk State University, pr. Lenina 33, Petrozavodsk, 185910, Russia

    Ya. P. Nizhnik & V. P. Andreev

  2. Karelian Research Center, Russian Academy of Sciences, ul. Pushkinskaya 11, Petrozavodsk, 185910, Russia

    B. Z. Belashev

Authors
  1. Ya. P. Nizhnik
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  2. V. P. Andreev
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  3. B. Z. Belashev
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Correspondence to V. P. Andreev.

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Original Russian Text © Ya.P. Nizhnik, V.P. Andreev, B.Z. Belashev, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1851–1857.

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Nizhnik, Y.P., Andreev, V.P. & Belashev, B.Z. Molecular complexes of 4-nitropyridine and 4-nitroquinoline N-oxides with boron trifluoride and hydrogen chloride as intermediates in SNAr reactions. Russ J Org Chem 44, 1824–1830 (2008). https://doi.org/10.1134/S1070428008120191

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  • DOI: https://doi.org/10.1134/S1070428008120191

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