Gas-Phase Acidities of Alcohols

Journal of the American Chemical Society

Volumn 92, Issue 20, 1970, Pages 5986-5992

  Brauman, John I ^a   Biairlb, Larry K ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947294759     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00723a029     Document Type: Article

References (55)

1. L. P. Hammett, “Physical Organic Chemistry,” McGraw-Hill, New York, N. Y., 1940.
2. G. E. K. Branch and M. Calvin, “The Theory of Organic Chemistry,” Prentice-Hall, Englewood Cliffs, N. J., 1941.
3. For some interesting comments see C. D. Ritchie and R. Uschold, J. Amer. Chem. Soc., 90, 2821 (1968).
4. J. D. Baldeschwieler, Science, 159, 263 (1968).
5. See J. I. Brauman and L. K. Blair, J. Amer. Chem. Soc., 90, 6561 (1968), for a preliminary report.
6. L. R. Anders, J. L. Beauchamp, R. C. Dunbar, and J. D. Baldeschwieler, J. Chem. Phys., 45, 1062 (1966).
7. J. L. Beauchamp, L. R. Anders, and J. D. Baldeschwieler, J. Amer. Chem. Soc., 89, 4569 (1967).
8. J. L. Beauchamp and S. E. Buttrill, Jr., J. Chem. Phys., 48, 1783 (1968).
9. J. M. S. Henis, J. Amer. Chem. Soc., 90, 844 (1968).
10. J. I. Brauman and L. K. Blair, J. Amer. Chem. Soc., 90, 5636 (1968).
11. See R. N. Compton and L. G. Christophorou, Phys. Rev., 154, 110 (1967), and references cited therein.
12. J. A. D. Stockdale, R. N. Compton, and P. W. Reinhardt, Phys. Rev., 184, 81 (1969).
13. V. L. von Trepka, Z. Naturforsch., A, 18, 1122 (1968).
14. D. Vogt and H. Neuert, Z. Phys., 199, 32 (1967).
15. See Advan. Chem. Ser., No. 58 (1966), especially the articles by J. H. Futrell and F. P. Abramson and by L. Friedman for reviews, discussions, and relevant comments.
16. S. W. Benson, “Thermochemical Kinetics,” Wiley, New York, N. Y., 1968.
17. J. C. McCoubrey, Trans. Faraday Soc., 51, 743 (1955).
18. A. Streitwieser, Jr., and J. H. Hammons, Progr. Phvs. Org. Chem., 3, 41 (1965).
19. However, see J. I. Brauman and K. C. Smvth, J. Amer. Chem. Soc., 91, 7778 (1969).
20. J. A. Kerr, Chem. Rev., 66, 465 (1966).
21. S. W. Benson, J. Chem. Educ., 42, 502 (1965).
22. R. S. Berry and C. W. Riemann, J. Chem. Phys., 38, 1540 (1963).
23. S. W. Benson and R. Shaw, Advan. Chem. Ser., No. 75, 288 (1968).
24. J. M. Williams and W. H. Hamill, J. Chem. Phys., 49, 4467 (1968).
25. 23
26. L. M. Branscomb, Phys. Rev., 48, 11 (1966).
27. J. Kay and F. M. Page, Trans. Faraday Soc., 62, 3081 (1966).
28. R. Walsh, D. M. Golden, and S. W. Benson, J. Amer. Chem. Soc., 88, 650 (1966). Propylene is also a strong acid, falling between methanol and water, probably for the same reason—a weak OH bond.
29. See J. I. Brauman and L. K. Blair, manuscript submitted for publication, for a general discussion of periodic trends.
30. See M. J. S. Dewar, Tetrahedron, 17, 123 (1962).
31. P. R. von Schleyer and C. W. Woodworth, J. Amer. Chem. Soc., 90, 6528 (1968).
32. and references cited therein. Also, see E. M. Arnett and J. W. Larsen, J. Amer. Chem. Soc., 91, 1438 (1969).
33. W. M. Schubert and D. F. Gurka, J. Amer. Chem. Soc., 91, 1443 (1969).
34. A. Himoe and L. M. Stock, J. Amer. Chem. Soc., 91, 1452 (1969).
35. See, for example M. J. S. Dewar, “Hyperconjugation,” Ronald Press, New York, N. Y., 1962.
36. see J. A. Pople and M. Gordon, J. Amer. Chem. Soc., 89, 4253 (1967).
37. M. D. Newton and W. N. Lipscomb, J. Amer. Chem. Soc., 89, 4261 (1967), for a different view of the origin of the dipole moment in methylacetylene.
38. M. S. B. Munson, J. Amer. Chem. Soc., 87, 2332 (1965).
39. H. Jaffe, Chem. Rev., 53, 191 (1953).
40. J. E. Leffler and E. Grunwald, “Rates and Equilibria of Organic Reactions,” Wiley, New York, N. Y., 1963.
41. J. I. Brauman and L. K. Blair, unpublished results.
42. J. Hine and M. Hine, J. Amer. Chem. Soc., 74, 5266 (1952).
43. P. Ballinger and F. H. Long, J. Amer. Chem. Soc., 82, 795 (1960).
44. J. I. Brauman and L. K. Blair, J. Amer. Chem. Soc., 91, 2126 (1969).
45. This proposal has been suggested previously as an explanation for effects of alkyl groups. For example, see W. M. Schubert, R. B. Murphy, and J. Robins, Tetrahedron, 17, 199 (1962).
46. T. L. Brown, J. Amer. Chem. Soc., 81, 3229, 3232 (1959).
47. S. W. Benson and A. N. Bose, J. Chem. Phys., 39, 3463 (1963).
48. G. Gioumousis and D. P. Stevenson, J. Chem. Phys., 29, 294 (1958).
49. J. D. Hirschfelder, C. F. Curtiss, and R. B. Bird, “Molecular Theory of Gases and Liquids,” Wiley, New York, N. Y., 1964, p 947.
50. K. G. Denbigh, Trans. Faraday Soc., 36, 936 (1940).
51. C. A. Coulson, A. Maccoll, and L. E. Sutton, Trans. Faraday Soc., 48, 106 (1952).
52. T. P. Lewis, Tetrahedron, 25, 4117 (1969).
53. N. C. Baird, Can. J. Chem., 47, 2306 (1969).
54. L. C. Allen and P. A. Kollman, Science, 167, 1443 (1970).
55. A. I. Vogel, “Practical Organic Chemistry,” 3rd ed, Wiley, New York, N. Y., 1966, p 877.