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Evaluation of hydrogen bonding ability of liquids and solids by C-13 NMR. Silica gel as a strong hydrogen bond donor

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Abstract

The chemical shift difference between signals of C(β) and C(α) of unsaturated ketones, Δδ, which we used before to measure acid strengths, has now been used to evaluate the hydrogen bond donor ability of solvents which are not acidic enough to hydronate the indicator. For such solvents there is no general correlation between H-bond donor ability and acid strength: hexa-fluoroisopropanol is a much weaker acid than acetic acid, but it is a stronger H-bond donor. The method can be applied to evaluate the H-bonding properties of solid surfaces, and it was thus found that silica gel has a much stronger H-bond donor ability than methanol or acetic acid.

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References

  1. D. Farcaşiu, A. Ghenciu and G. Miller, J. Catal. 134 (1992) 118.

    Google Scholar 

  2. D. Farcaşiu and A. Ghenciu, J. Am. Chem. Soc. 115 (1993) 10901.

    Google Scholar 

  3. J.F. Bunnett and R.A.Y. Jones, Pure Appl.Chem. 60 (1988) 1115.

    Google Scholar 

  4. B.P. Dailey and J.N. Shoolery, J. Am. Chem. Soc. 77 (1955) 3977.

    Google Scholar 

  5. J.T. Edward, J.B. Leane and I.C. Wang, Can. J. Chem. 40 (1962) 1521.

    Google Scholar 

  6. D.G. Lee, Can. J. Chem. 48 (1970) 1919.

    Google Scholar 

  7. D. Farcaşiu and A. Ghenciu, J. Org. Chem. 56 (1991) 6050.

    Google Scholar 

  8. D. Farcaşiu and A. Ghenciu, J. Catal. 134 (1992) 126.

    Google Scholar 

  9. P.E. Eaton, G.R. Carlson and J.T. Lee, J. Org. Chem. 38 (1973) 4071.

    Google Scholar 

  10. D. Farcaşiu and H. Cao, J. Mol. Catal. 87 (1994) 215.

    Google Scholar 

  11. D. Farcaşiu and J.Q. Li, J. Phys. Chem. 98 (1994) 6893.

    Google Scholar 

  12. D. Farcaşiu and J.Q. Li, J. Catal., in print.

  13. D.L. Hughes, J. Phys. Org. Chem., in print.

  14. T. Xu, E.J. Munson and J.F. Haw, J. Am. Chem. Soc. 116 (1994) 1962.

    Google Scholar 

  15. D. Fřcaşiu, S.L. Fisk, M.T. Melchior and K.D. Rose, J. Org. Chem 47 (1982) 453.

    Google Scholar 

  16. D.L. Vander Hart, W.L. Earl and A.N. Garroway, J. Magn. Res. 44 (1981) 361

    Google Scholar 

  17. A. Pines, M.G. Gibby and J.S. Waugh, J. Chem. Phys. 59 (1973) 569.

    Google Scholar 

  18. A.S. Tracey, B. Gallefi and S. Mahjour, Can. J. Chem. 66 (1988) 2294.

    Google Scholar 

  19. D. Farcaşiu, J. Jähme and C. Rüchardt, J. Am. Chem. Soc. 107 (1985) 5717.

    Google Scholar 

  20. D. Farcaşiu, US Patents 4,585,750 (1986); 4,673,769 (1987); 4,677,090 (1987).

  21. Handbook of Chemistry and Physics, 72rd Ed. (CRC Press, Boca Raton, 1991) (a) p. 8–39; (b) p. 8–14.

  22. A. McKillop and D.W. Young, Synthesis (1979) 401;

  23. K. Smith, ed.,Solid Supports and Catalysts in Organic Synthesis, Organic Chemistry Series (Horwood PTR Prentice Hall, 1992) pp. 95–96.

  24. H.A. Benesi, J. Am. Chem. Soc. 78 (1956) 5490

    Google Scholar 

  25. K. Tanabe,Solids Acids and Bases — Their Catalytic Properties (Kodansha/Academic Press, Tokyo/New York) p. 2.

  26. B.W. Wojciechowski, Catal. Rev. Sci. Eng. 30 (1988) 629

    Google Scholar 

  27. M.A. Vannice, J. Catal. 37 (1975) 462.

    Google Scholar 

  28. H.-F. Liu, R.-S. Liu, K.Y. Liew, R.E. Johnson and J.H. Lunsford, J. Am. Chem. Soc. 106 (1984) 4117;

    Google Scholar 

  29. K.J. Zhen, M.M. Khan, C.H. Mak, K.B. Lewis and G.A. Somorjai, J. Catal. 94 (1985) 501.

    Google Scholar 

  30. V.D. Drăguţan, A.T. Balaban and M. Dimonie,Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins (Wiley Interscience, New York, 1985).

    Google Scholar 

  31. S.D. Robertson, B.D. McNicol, J.H. de Baas, S.C. Kloet and J.W. Jenkins, J. Catal. 37 (1975) 424

    Google Scholar 

  32. G. Galleher, J.G. Goodwin, Jr., C.-S. Huang and M. Houalla, J. Catal. 127 (1991) 719; 140 (1993) 453.

    Google Scholar 

  33. P. Schindler and H.R. Kamber, Helv. Chim. Acta 51 (1968) 1781

    Google Scholar 

  34. D.N. Strazhesko, V.B. Strelko, V.N. Belyakov and C. Rubank, J. Chromatography 102 (1974) 191

    Google Scholar 

  35. M.L. Hair and W. Hertl, J. Phys. Chem. 74 (1970) 91.

    Google Scholar 

  36. K. Tanabe, M. Misono, Y. Ono and H. Hattori, in:New Solid Acids and Bases — Their Catalytic Properties, Studies in Surface Science and Catalysis, eds. B. Delmon and J.T. Yates (Kodansha/Elsevier, Tokyo/Amsterdam, 1989) pp. 93–102.

    Google Scholar 

  37. E.P. Parry, J. Catal. 2 (1963) 371.

    Google Scholar 

  38. J.E. Mapes and R.R. Eischens, J. Phys. Chem. 58 (1954) 809.

    Google Scholar 

  39. T. Yamaguchi and K. Tanabe, Bull. Chem. Soc. Jpn. 47 (1974) 424

    Google Scholar 

  40. K. Shibata, T. Kiyoura, J. Kitagawa, T. Sumyioshi and K. Tanabe, Bull. Chem. Soc. Jpn. 46 (1973) 2985.

    Google Scholar 

  41. C. Rochester,Acidity Functions, Organic Chemistry Series, Vol. 17 (Academic Press, NewYork, 1970) p. 22.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemical and Petroleum Engineering, University of Pittsburgh, 1249 Benedum Hall, 15261, Pittsburgh, PA, USA

    Dan Farcaşiu & Anca Ghenciu

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  1. Dan Farcaşiu
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  2. Anca Ghenciu
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Farcaşiu, D., Ghenciu, A. Evaluation of hydrogen bonding ability of liquids and solids by C-13 NMR. Silica gel as a strong hydrogen bond donor. Catal Lett 31, 351–358 (1995). https://doi.org/10.1007/BF00808599

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  • DOI: https://doi.org/10.1007/BF00808599

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