Acid strength of tetrafluoroboric acid: The hydronium ion as a superacid and the inapplicability of water as an indicator of acid strength

Journal of the Chemical Society - Faraday Transactions

Volumn 93, Issue 12, 1997, Pages 2161-2165

  Fǎrcaşiu, Dan ^a   Hâncu, Dan ^a  

^a University of Pittsburgh   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748596871     PISSN: 09565000     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700798a     Document Type: Article

References (79)

1. (a) D. A. McCaulay, B. H. Shoemaker and A. P. Lien, Ind. Eng. Chem., 1950, 43, 2103;
2. (b) M. Kilpatrick and F. E. Luborsky, J. Am. Chem. Soc., 1953, 75, 577.
3. C. Reid, J. Am. Chem. Soc., 1954, 76, 3264.
4. (a) D. A. McCaulay and A. P. Lien, J. Am. Chem. Soc., 1951, 73, 2013;
5. (b) E. L. Mackor, A. Hofstra and J. H. van der Waals, Trans. Faraday Soc., 1958, 54, 186.
6. P. Pfeiffer and R. Wizinger, Liebigs Ann. Chem., 1928, 461, 132.
7. C. MacLean and E. L. Mackor, Discuss. Faraday Soc., 1962, 34, 165.
8. (a) R. Gut and K. Gautschi, J. Inorg. Nucl. Chem., (Hyman Mem. Vol.), 1976, 95;
9. (b) J. Devynck, A. Ben Hadid, P-L. Fabre and B. Tremillon, Anal. Chim. Acta, 1978, 100, 343.
10. (a) L. P. Hammett and A. J. Deyrup, J. Am. Chem. Soc., 1932, 54, 2721;
11. (b) L. P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, 2nd edn., 1970;
12. (c) C. H. Rochester, Acidity Functions, Organic Chemistry Monographs, ed. Blomquist, Academic Press, New York, 1970, vol. 17.
13. G. A. Olah, G. K. Surya Prakash and J. Sommer, Superacids, Wiley-Interscience, New York, 1985, p. 9.
14. J. Bessiere, Anal. Chim. Acta, 1970, 52, 55.
15. (a) E. C. Hughes and S. M. Darling, Ind. Eng. Chem., 1951, 43, 746;
16. (b) M. Kilpatrick and F. E. Luborsky, J. Am. Chem. Soc., 1954, 76, 5865.
17. S. Pawlenko, Z. Anorg. Allg. Chem., 1965, 334, 292.
18. H. C. Brown and H. Pearsall, J. Am. Chem. Soc., 1951, 73, 4081.
19. D. Fǎrcaşiu and A. Ghenciu, Prog. NMR Spectrosc., 1996, 29, 129.
20. (a) D. Fǎrcaşiu, S. L. Fisk, M. T. Melchior and K. D. Rose, J. Org. Chem., 1982, 47, 453;
21. (b) D. Fǎrcaşiu, Acc. Chem. Res., 1982, 15, 46;
22. (c) D. Fǎrcaşiu, G. Marino, G. Miller and R. V. Kastrup, J. Am. Chem. Soc., 1989, 111, 7210.
23. S. Pawlenko, Z. Anorg. Allg. Chem., 1962, 315, 291.
24. J. F. Bunnett and R. A. Y. Jones, Pure Appl. Chem., 1989, 60, 1115.
25. S. Pawlenko, Z. Anorg. Allg. Chem., 1964, 328, 133.
26. M. Stacey, J. C. Tatlow and A. G. Sharpe, Advances in Fluorine Chemistry, Butterworths, London, 1960, ch. 3.
27. (a) A. Ghenciu, MS Thesis, University of Pittsburgh, 1994;
28. 4 in much more dilute solutions was studied by C. A. Wamser, J. Am. Chem. Soc., 1948, 70, 1209;
29. C. A. Wamser, J. Am. Chem. Soc., 1951, 73, 409.
30. R. J. Gillespie and J. Liang, J. Am. Chem. Soc., 1988, 110, 6053.
31. (a) D. Fǎrcaşiu, A. Ghenciu and G. Miller, J. Catal., 1992, 134, 118;
32. (b) D. Fǎrcaşiu and A. Ghenciu, J. Am. Chem. Soc., 1993, 115, 10901.
33. (a) D. Fǎrcaşiu and A. Ghenciu, J. Catal., 1992, 134, 126;
34. (b) D. Fǎrcaşiu and H. Cao, J. Mol. Catal., 1994, 87, 215;
35. (c) D. Fǎrcaşiu and J. Q. Li, J. Phys. Chem., 1994, 98, 6893;
36. (d) D. Fǎrcaşiu and J. Q. Li, J. Catal., 1995, 152, 198;
37. (e) D. L. Hughes, J. Phys. Org. Chem., 1994, 7, 625.
38. D. Fǎrcaşiu and A. Ghenciu, Catal. Lett., 1995, 31, 351.
39. Standard Methods of Chemical Analysis, ed. F. J. Welcher, Nostrand Reinhold, New York, 6th edn., 1973, vol. 2, part A, p. 574.
40. K. Yates and H. Wai, J. Am. Chem. Soc., 1964, 86, 5408.
41. (a) J. H. Ridd, personal communication;
42. (b) M. Sampoli, N. C. Marziano and C. Tortato, J. Phys. Chem., 1989, 93, 7532;
43. (c) N. C. Marziano, Org. Reactivity, 1996, 30, 29.
44. (a) K. N. Bascombe and R. P. Bell, Discuss. Faraday Soc., 1957, 24, 158;
45. (b) H. D. Beckey, Z. Naturforsch. A, 1959, 14, 712;
46. H. D. Beckey, Z. Naturforsch. 1960, 15, 822;
47. (c) P. F. Knewstubb and A. W. Tickner, presented at the Meeting on Mass Spectrometry, ASTM, Atlantic City, 1960;
48. (d) M. Eigen, Angew. Chem., 1963, 75, 489.
49. J. N. Bronsted and E. A. Guggenheim, J. Am. Chem. Soc., 1927, 49, 2554.
50. H. Lemaire and H. J. Lucas, J. Am. Chem. Soc., 1951, 73, 5198.
51. L. P. Hammett and M. A. Paul, J. Am. Chem. Soc., 1934, 56, 827.
52. A. Albert and E. P. Serjeant, The Determination of Ionization Constants, Chapman and Hall, London, 1984, p. 162.
53. J. E. Macintyre, Dictionary of Inorganic Compounds, Chapman and Hall, London, 1992, vol. 2, p. 3364.
54. A value of -3.25 was deduced in: P. A. H. Wyatt, Discuss. Faraday Soc., 1957, 24, 161
55. (a) C. D. Nenitzescu and I. P. Cantuniari, Ber. Dtsch. Chem. Ges., 1933, 66, 1097;
56. (b) C. D. Nenitzescu, M. Avram and E. Sliam, Bull. Soc. Chim. France, 1955, 1266.
57. (a) R. M. Roberts, J. Am. Chem. Soc., 1957, 79, 5484;
58. (b) C. D. Nenitzescu, I. Necsoiu, A. Glatz and M. Zalman, Chem. Ber., 1959, 92, 10.
59. A. Schneider, R. W. Warren and E. J. Janoski, J. Org. Chem., 1966, 31, 1617.
60. (a) T. Gramstad and R. N. Haszeldine, J. Chem. Soc., 1957, 4069;
61. (b) J. B. Spencer and J. O. Lundgren, Acta Crystallogr., Sect. 3, 1973, 29, 1923;
62. (c) R. D. Howells and J. D. McCown, Chem. Rev., 1977, 77, 69.
63. E. M. Arnett and C. Y. Wu, J. Am. Chem. Soc., 1962, 84, 1680.
64. Discussions in Catalytic Chemistry. I. Catalysis by Strong Solid Acids (Post-congress workshop after the 11th International Congress on Catalysis), Baltimore, MD, USA, 6-7 July 1996.
65. M. Hunger, D. Freude and H. Pfeifer, J. Chem. Soc., Faraday Trans., 1991, 87, 657.
66. (a) P. Batamack, C. Dorémieux-Morin, J. Fraissard and D. Freude, J. Phys. Chem., 1991, 95, 3790;
67. (b) L. Heeribout, V. Semmer, P. Batamack, C. Dorémieux-Morin, R. Vincent and J. Fraissard, Stud. Surf. Sci. Catal, 1996, 101, 831;
68. (c) for the method, see: C. Dorémieux-Morin, J. Magn. Reson., 1976, 21, 419, and subsequent papers.
69. T. Xu, E. J. Munson and J. F. Haw, J. Am. Chem. Soc., 1994, 116, 1962.
70. (a) A. Zecchina, R. Buzzoni, S. Bordiga, F. Geobaldo, D. Scarano, G. Ricchiardi and G. Spoto, Stud. Surf. Sci. Catal., 1995, 97, 213;
71. (b) F. Wakabayashi, J. N. Kondo, K. Domen and C. Hirose, J. Phys. Chem., 1996, 100, 1442;
72. (c) A. Zecchina, F. Geobaldo, G. Spoto, S. Bordiga, G. Ricchiardi, R. Buzzoni and G. Petrini, J. Phys. Chem., 1996, 100, 16584.
73. (a) F. Haase and J. Sauer, J. Am. Chem. Soc., 1995, 117, 3780;
74. (b) M. Krossner and J. Sauer, J. Phys. Chem., 1996, 100, 6199;
75. (c) J. Sauer, Science, 1996, 271, 774;
76. (d) R. van Santen and G. J. Kramer, Chem. Rev., 1995, 95, 637;
77. (e) S. A. Zygmunt, L. A. Curtiss, L. E. Iton and M. K. Erhardt, J. Phys. Chem., 1996, 100, 6663.
78. L. Smith, A. K. Cheetham, R. E. Morris, L. Marchese, J. M. Thomas, P. A. Wright and J. Chen, Science, 1996, 271, 799.
79. (a) K. Domen (Tokyo Inst. of Technology), at the meeting of ref. 39; (b) T. Fujino, M. Kashitani, S. S. Kano, F. Wakabayashi, F. Goto, M. Ishida, A. Wada, K. Domen and C. Hirose, in preparation.