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peri-Naphthylenediamines

23. Investigation of the intramolecular hydrogen bond in protonated 1,8-bis(dimethylamino)naphthalenes by1H NMR spectroscopy

  • Physical Chemistry
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Abstract

The1H NMR spectra of protonated 1,8-bis(dimethylamino)naphthalene cations (“proton sponges”) containing substituents of various types in positions 2(7) and 4(5) were measured. To estimate the degree of asymmetry of the intramolecular hydrogen bridge in the cations studied, the spin-spin coupling constants of the NH proton with protons of nonequivalent Me2N groups were suggested to be used. Bromination of the “proton sponge” into positions 2 and 7 byN-bromosuccinimide was carried out for the first time.

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References

  1. V. A. Ozeryanskii and A. F. Pozharskii,Izv. Akad. Nauk, Ser. Khim., 1997, 1501 [Russ. Chem. Bull., 1997,46, 1437 (Engl. Transl.)].

    Google Scholar 

  2. F. Hibbert,J. Chem. Soc., Perkin Trans. 2, 1974, 1862.

  3. A. F. Pozharskii, A. N. Suslov, N. M. Starshikov, L. L. Popova, N. A. Klyuev, and V. A. Adanin,Zh. Org. Khim., 1980,16, 2216 [J. Org. Chem. USSR, 1980,16 (Engl. Transl.)].

    CAS  Google Scholar 

  4. H. A. Staab and T. Saupe,Angew. Chem., Int. Ed. Engl., 1988,27, 865.

    Article  Google Scholar 

  5. A. L. Llamas-Saiz, C. Foces-Foces, and J. Elguero,J. Mol. Struct., 1994,328, 297.

    Article  CAS  Google Scholar 

  6. Z. Dega-Szafran, B. Nowak-Wydra, and M. Szafran,Magn. Res. Chem., 1993,31, 726.

    Article  CAS  Google Scholar 

  7. Z. Malarski, L. Sobczyk, and E. Grech,J. Mol. Struct., 1988,17, 339.

    Article  Google Scholar 

  8. B. Brzezinski, E. Grech, Z. Malarski, and L. Sobczyk,J. Chem. Soc., Faraday Trans., 1990,86, 1777.

    Article  CAS  Google Scholar 

  9. B. Brycki, B. Brzezinsky, E. Grech, Z. Malarski, and L. Sobczyk,Magn. Res. Chem., 1991,29, 558.

    Article  CAS  Google Scholar 

  10. L. Jaroszewski, B. Lesyng, J. J. Tanner, and J. A. McCammon,Chem. Phys. Lett., 1990,175, 282.

    Article  CAS  Google Scholar 

  11. A. F. Pozharskii,Usp. Khim., 1998,67, 3 [Russ. Chem. Rev., 1998,67, 1 (Engl. Transl.)].

    CAS  Google Scholar 

  12. J. A. Kanters, A. Schouten, A. J. M. Duisenberg, T. Glowiak, Z. Malarski, L. Sobczyk, and E. Grech,Acta Crystallogr., C, 1991,47, 2148.

    Article  Google Scholar 

  13. J. A. Kanters, E. H. ter Horst, J. Kroon, and E. Grech,Acta Crystallogr., C, 1992,48, 328.

    Article  Google Scholar 

  14. A. F. Pozharskii, V. V. Kuz'menko, G. G. Aleksandrov, and D. V. Dmitrienko,Zh. Org. Khim., 1995,31, 570 [Russ. J. Org. Chem., 1995,31 (Engl. Transl.)].

    CAS  Google Scholar 

  15. V. A. Ozeryanskii, A. F. Pozharskii, and N. V. Vistorobskii,Zh. Org. Khim., 1997,33, in press [Russ. J. Org. Chem., 1997,33, in press (Engl. Transl.)].

  16. N. V. Vistorobskii and A. F. Pozharskii,Zh. Org. Khim., 1989,25, 2154 [J. Org. Chem. USSR, 1989,25 (Engl. Transl.)].

    CAS  Google Scholar 

  17. S. Toppet, K. Platteborze, and T. Zeegers-Huyskens,J. Chem. Soc., Perkin Trans. 2, 1995, 831.

  18. H. J. G. Yah, M. Soto, and I. Morishima,J. Magn. Reson., 1977,26, 365.

    Google Scholar 

  19. Correlation Analysis in Chemistry: Recent Advances, Eds. N. B. Chapman and J. Shorter, Plenum Press, New York-London, 1978.

    Google Scholar 

  20. V. Balasubramaniyan,Chem. Rev., 1966,66, 567.

    Article  CAS  Google Scholar 

  21. The Chemistry of the Amino Group, Ed. S. Patai, Interscience Publ., London-New York-Sydney, 1968, 161.

    Google Scholar 

  22. B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov, inYaMR-spektroskopiya v organicheskoi khimii [NMR Spectroscopy in Organic Chemistry], Khimiya, Leningrad, 1983, 56 (in Russian).

    Google Scholar 

  23. H. A. Staab, M. A. Zirnstein, and C. Krieger,Angew. Chem., Int. Ed. Engl., 1989,28, 86.

    Article  Google Scholar 

  24. A. F. Pozharskii, N. L. Chikina, N. V. Vistorobskii, and V. A. Ozeryanskii,Zh. Org. Khim., 1997,33, in press [Russ. J. Org. Chem., 1997,33, in press (Engl. Transl.)].

  25. E. M. Arnett, inProgress in Physical Organic Chemistry, Eds. S. G. Cohen, A. Streitwieser, and R. W. Taft, Interscience Publ., New York-London, 1963.

    Google Scholar 

  26. N. V. Vistorobskii and A. F. Pozharskii,Izv. Akad. Nauk, Ser. Khim., 1996, 2297 [Russ. Chem. Bull., 1996,45, 2181 (Engl. Transl.)].

    Google Scholar 

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For Part 22, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 68–75, January, 1998.

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Pozharskii, A.F., Ozeryanskii, V.A. peri-Naphthylenediamines. Russ Chem Bull 47, 66–73 (1998). https://doi.org/10.1007/BF02495511

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  • DOI: https://doi.org/10.1007/BF02495511

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