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Absence of correlation of hydrogen bond donor ability with acid strength and catalytic activity of acid catalysts

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Abstract

Two liquids, acetic acid and hexafluoroisopropanol (HFIP), and two solids, silica gel and polymethacrylic acid (PMA), were compared for hydrogen bond donor ability, acid strength, and catalytic activity in typical acid‐catalyzed reactions, inversion of sugar and cleavage of acetone dimethyl ketal. In each pair, the weaker acid (HFIP and silica gel, respectively) was much the stronger hydrogen bond donor, but was totally devoid of catalytic activity, which the poor hydrogen bond donor but stronger acids (acetic and methacrylic acid, respectively) exhibited. A strong hydrogen bond donor (e.g., HFIP) enhances, however, the catalytic activity of the acid catalyst (AcOH). Thus, hydrogen bond donor ability is not a measure of acid strength. A correlation of the two properties is possible only when each group (acids and bases) involved in the comparison consists of very close structural relatives. Such a correlation cannot be extrapolated to any other case.

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References

  1. J.N. Brønsted and K. Pedersen, Z. Physik. Chem. 108 (1923) 185

    Google Scholar 

  2. M. Eigen, Angew. Chem. 75 (1963) 489.

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  4. D. FĂcaşiu, A. Ghenciu and J.Q. Li, J. Catal. 158 (1996) 116.

    Article  Google Scholar 

  5. H.A. Benesi and B.H.C. Winquist, in: Advances in Catalysis, Vol. 27, eds. D. Eley, H. Pines and P.B. Weisz (Academic Press, New York, 1978) p. 97

    Google Scholar 

  6. W.E. Farneth and R.J. Gorte, Chem. Rev. 95 (1995) 615

    Article  CAS  Google Scholar 

  7. D. FĂrcaşiu and A. Ghenciu, Progr. NMR Spectroscopy 29 (1996) 129.

    Article  Google Scholar 

  8. D. FĂrcaşiu and D. HĂncu, J. Chem. Soc. Faraday Trans. 93 (1997) 2161.

    Article  Google Scholar 

  9. H.S. Bloch, H. Pines and L. Schmerling, J. Am. Chem. Soc. 68 (1946) 153

    Article  CAS  Google Scholar 

  10. C.D. Nenitzescu, M. Avram and E. Sliam, Bull. Soc. Chem. France (1955) 1266

  11. J.M. Oelderik, cited in: D.M. Brouwer and E.L. Mackor, Proc. Chem. Soc. (1964) 147

  12. J.M. Oelderik, E.L. Mackor, J.C. Platteeuw and A. van der Wiel, Brit. Patent 981311 (1962); see also US Patent 3201494 (1965)

  13. D.M. Brouwer and H. Hogeveen, Progr. Phys. Org. Chem. 9 (1972) 179.

    CAS  Google Scholar 

  14. H. Hogeveen and A.F. Bickel, Chem. Commun. 635 (1967)

  15. G.A. Olah and J. Lukas, J. Am. Chem. Soc. 89 (1967) 2227, 4739.

    Article  CAS  Google Scholar 

  16. G.A. Olah, G.K.S. Surya-Prakash and J. Sommer, Superacids(Wiley-Interscience, New York, 1985).

    Google Scholar 

  17. M.M. Davis, Acid-Base Behavior in Aprotic Organic Solvents, NBS Monograph, Vol. 105 (National Bureau of Standards, Washington, DC, 1968).

    Google Scholar 

  18. D. FĂrcaşiu, J. Catal. 160 (1966) 309.

    Google Scholar 

  19. A. Zecchina, R. Buzzoni, S. Bordiga, F. Geobaldo, D. Scarano, G. Ricchiardi and G. Spoto, in: Zeolites: A Refined Tool for Designing Catalytic Sites, Proc. Int. Zeolite Symp., Quebec, 1995, eds. L. Bonneviot and S. Kaliaguine (Elsevier, Amsterdam 1995) p. 213

    Google Scholar 

  20. R. Buzzoni, S. Bordiga, G. Ricchiardi, C. Lamberti and A. Zecchina, Langmuir 12 (1996) 930

    Article  CAS  Google Scholar 

  21. A. Zecchina, F. Geobaldo, G. Spoto, S. Bordiga, G. Ricchiardi, R. Buzzoni and G. Petrini, J. Phys. Chem. 100 (1996) 16584

    Article  CAS  Google Scholar 

  22. A. Zecchina, S. Bordiga, G. Spoto, D. Scarano, G. Spano and F. Geobaldo, J. Chem. Soc. Faraday Trans. 92 (1996) 4863.

    Article  Google Scholar 

  23. D.-FĂrcaşiu, J. Catal. 167 (1997) 303

    Article  Google Scholar 

  24. D. FĂrcaşiu and D. HĂncu, Abstr. P55 presented at the 15th Meeting of the North American Catal. Soc., Chicago, IL, 19 May 1997.

  25. D. FĂrcaşiu and A. Ghenciu, Catal. Lett. 31 (1995) 351

    Article  Google Scholar 

  26. A. Ghenciu, Ph.D. thesis, University of Pittsburgh (1996).

  27. Handbook of Chemistry and Physics, 72nd Ed. (CRC Press, Boca Raton, FL, 1991) pp. 8-39.

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. D. FĂrcaşiu, A. Ghenciu, G. Marino and K.D. Rose, J. Am. Chem. Soc. 119 (1997) 11826.

    Article  Google Scholar 

  31. F.A. Long and M.A. Paul, Chem. Rev. 57 (1957) 965.

    Article  Google Scholar 

  32. P.M. Leminger and M. Kilpatrick, J. Am. Chem. Soc. 60 (1938) 2891.

    Article  Google Scholar 

  33. D. FĂrcaşiu, A. Ghenciu, G. Marino and R.V. Kastrup, J. Mol. Catal. 126 (1997) 141.

    Article  Google Scholar 

  34. D. FĂrcaşiu, J. Jähme and C. Rüchardt, J. Am. Chem. Soc. 107 (1985) 5717, and references therein.

    Article  Google Scholar 

  35. G. Bodamer and R. Kunin, Ind. Eng. Chem. Int. Ed. 43 (1951) 1082.

    Article  CAS  Google Scholar 

  36. P.J. Kropp, K.A. Daus, S.D. Crawford, M.W. Tubergen, K.D. Kepler, S.L. Craig and V.P. Wilson, J. Am. Chem. Soc. 112 (1990) 7433, and subsequent papers.

    Article  CAS  Google Scholar 

  37. D. FĂrcaşiu, in: Nucleophilicity, Advances in Chemistry Series, Vol. 215, eds. J.M. Harris and S.P. McManus (American Chemical Society, Washington, DC, 1987) chapter 20.

    Google Scholar 

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

    Dan Fărcaşiu & Dan Hâncu

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  1. Dan Fărcaşiu
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  2. Dan Hâncu
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Fărcaşiu, D., Hâncu, D. Absence of correlation of hydrogen bond donor ability with acid strength and catalytic activity of acid catalysts. Catalysis Letters 53, 3–6 (1998). https://doi.org/10.1023/A:1019068814279

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