Conjugative interaction in styrenes

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 10947-10955

  Von Doering, W E ^a   Benkhoff, Johannes ^a   Carleton, Peter Smart ^a   Pagnotta, Marco ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE DERIVATIVE;

ARTICLE; CONJUGATION; ENTHALPY; THERMODYNAMICS;

EID: 0003913222     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971040e     Document Type: Article

References (73)

1. Pagnotta, M. Conjugative Interaction in Olefins. Ph.D. Dissertation, Harvard University, 1984; Diss. Abstr. Intern. B 1985, 45, 2163 (Order No. 84-19388).
2. Carleton, Peter Smart, Conjugative Interaction of Benzene Rings and Double Bonds. Ph.D. Dissertation, Yale University, 1967; Diss. Abstr. Intern. B 1967, 27, 4265 (Order No. 67-07001).
3. Carleton, Peter Smart, Conjugative Interaction of Benzene Rings and Double Bonds. Ph.D. Dissertation, Yale University, 1967; Diss. Abstr. Intern. B 1967, 27, 4265 (Order No. 67-07001).
4. Pagnotta, M. Conjugative Interaction in Olefins. Ph.D. Dissertation, Harvard University, 1984; Diss. Abstr. Intern. B 1985, 45, 2163 (Order No. 84-19388).
5. Pagnotta, M. Conjugative Interaction in Olefins. Ph.D. Dissertation, Harvard University, 1984; Diss. Abstr. Intern. B 1985, 45, 2163 (Order No. 84-19388).
6. (a) Hine, J.; Skogland, M. J. J. Org. Chem. 1982, 47, 4766-4770 (further references therein),
7. (b) Hine, J. Structural Effects on Equilibria in Organic Chemistry; Wiley: New York, 1975; pp 122-126, 270-276.
8. (c) Hine, J.; Flachskam, N. W. J. Am. Chem. Soc. 1973, 95, 1179-1185.
9. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
10. Rogers, D. W.; McLafferty, F. J. Tetrahedron 1971, 21, 3765-3775.
11. 8
12. Williams, R. B. J. Am. Chem. Soc. 1942, 64, 1395-1404.
13. 0) of -3.33 kcal/ mol.
14. Roth, W. R.; Lennartz, H.-W.; Doering, W. v. E.; Birladeanu, L.; Guyton, C. A.; Kitagawa, T. J. Am. Chem. Soc. 1990, 112, 1722-1732.
15. H2, -59.82), from which conjugative interaction per phenyl vis-à-vis hydrogen becomes -2.0 or -1.83 kcal/mol. These values are almost identical with that resulting from replacement of vinyl hydrogen by alkyl, -2.01 kcal/ mol (cf. Figure 1), whence conjugative interaction in these examples might appear to be +0.18 ± 0.5 kcal/mol.
16. Compare Table 41 (p 1091) of ref 13, in which the value, -2.2 kcal/mol, is proposed.
17. Roth, W. R.; Staemmler, V.; Neumann, M.; Schmuck, C. Liebig's Ann. 1995, 1061-1118.
18. van't Hoff, J. H. Études de dynamique chimique, 1st ed.; Muller: Amsterdam, 1884.
19. Benson, S. W.; Bose, A. N. J. Am. Chem. Soc. 1963, 85, 1385-1387.
20. Taskinen, E.; Lindholm, N. J. Phys. Org. Chem. 1994, 7, 256-258.
21. Honegger, E.; Yans, Z.-z.; Heilbronner, E.; Doering, W. v. E.; Schmidhauser, J. C. Helv. Chim. Acta 1984, 67, 640-653.
22. Doering, W. v. E.; Schmidhauser, J. C. J. Am Chem. Soc. 1984, 106, 5025.
23. Roth, W. R.; Lennartz, H.-W.; Doering, W. v. E.; Dolbier, W. R., Jr.; Schmidhauser, J. C. J. Am Chem. Soc. 1988, 110, 1883-1889.
24. Rogers, D. W.; Crooks, E. L. J. Chem. Thermodyn. 1983, 15, 1087-1092. Rogers, D. W.; Crooks, E. L.; Dejroongruang, K. J. Chem. Thermodyn. 1987, 19, 1209-1215. Rogers, D. W.; Dejroongruang, K. J. Chem. Thermodyn. 1988, 20, 675-680.
25. Rogers, D. W.; Crooks, E. L. J. Chem. Thermodyn. 1983, 15, 1087-1092. Rogers, D. W.; Crooks, E. L.; Dejroongruang, K. J. Chem. Thermodyn. 1987, 19, 1209-1215. Rogers, D. W.; Dejroongruang, K. J. Chem. Thermodyn. 1988, 20, 675-680.
26. Rogers, D. W.; Crooks, E. L. J. Chem. Thermodyn. 1983, 15, 1087-1092. Rogers, D. W.; Crooks, E. L.; Dejroongruang, K. J. Chem. Thermodyn. 1987, 19, 1209-1215. Rogers, D. W.; Dejroongruang, K. J. Chem. Thermodyn. 1988, 20, 675-680.
27. Wiberg, K. B.; Wassermann, D. J.; Martin, E.; Murcko, M. A. J. Am. Chem. Soc. 1985, 107, 6019-6022.
28. Data involving tert-butyl and similarly sterically crowded groups have been omitted, but their inclusion would not have influenced the outcome.
29. Bateman, L.; Cunneen, J. I. J. Chem. Soc. 1951, 2283-2289.
30. Doering, W. v. E.; Bragole, R. Tetrahedron 1966, 22, 385-391.
31. (a) Wilson, S. T.; Osborn, J. A. J. Am. Chem. Soc. 1971, 93, 3068-3070.
32. (b) Bradley, J. S.; Wilkinson, G. Inorg. Synth. 1977, 17, 73-74.
33. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988; e.g., p 79.
34. 23
35. Dewar, M. J. S.; Schmeising, H. N. Tetrahedron 1959, 5, 166-178. Dewar, M. J. S.; Schmeising, H. N. Tetrahedron 1960, 9, 96-120.
36. Dewar, M. J. S.; Schmeising, H. N. Tetrahedron 1959, 5, 166-178. Dewar, M. J. S.; Schmeising, H. N. Tetrahedron 1960, 9, 96-120.
37. Cram, D. J. J. Am. Chem. Soc. 1949, 77, 3883-3889.
38. Fort, A. W.; Girard, C. A. J. Am. Chem. Soc. 1961, 83, 3449-3453.
39. (a) Franklin, J. L. Ind. Eng. Chem. 1949, 41, 1070-1076.
40. (b) Benson, S. W.; Cruikshank, F. R.; Golden, D. M.; Haugen, G. R.; O'Neal, H. E.; Rodgers, A. S.; Walsh, R. Chem. Rev. 1968, 68, 1513-1524.
41. (c) Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
42. fH° of rrans-l-phenylbutene-2 [1b(E)] is +24.32 ± 0.26 kcal/mol.
43. est(2c), respectively.
44. est of 3b and 3d of +5.65 and 7.17 kcal/mol, respectively. Mean values of+5.51 ± 0.21 and +7.22 ± 0.30 kcal/mol are included in Chart 1, series 3, row 4.
45. Roth, W. R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R. Chem. Ber. 1991, 124, 2499-2521.
46. Saïd, M.; Maynau, D.; Malrieu, J.-P.; Garcia Bach, M.-A. J. Am. Chem. Soc. 1984, 106, 571-579.
47. Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551-8566.
48. fH° by 0.75 kcal/mol, all others remaining unchanged.
49. "...it's one of those things that once you have done it with supervision of someone who really understands it, then you will understand it. But working from the literature, it is not so easy."
50. 41
51. For example: Gundertofte, K.; Liljefors, T.; Norrby, P.-O.; Pettersson, I. J. Comput. Chem. 1996, 17, 429-449.
52. Dewar, M. J. S. XXIIIrd International Congress of Pure and Applied Chemistry; Butterworths: London, 1971; Vol. 1, pp 1-30.
53. Proctor, George R., unpublished work on the 1-phenyl-3-mesityl-propene system; Yale University, 1963, supported by the Norman Fund.
54. Hine, J.; Skogland, M. J. J. Org. Chem. 1982, 47, 4758-4766.
55. Bushby, R. J.; Ferber, G. J. J. Chem. Soc., Perkin Trans. 2 1976, 1683-1688.
56. Cieplak, P.; Howard, A. E.; Powers, J. P.; Rychnovsky, S. D.: Kollman, P. A. J. Org. Chem. 1996, 61, 3662-3668.
57. Johnson, J.; Schwartz, A.; Jacobs, T. L. J. Am. Chem. Soc. 1938, 60, 1882-1884.
58. Grovenstein, E.; Lee, D. E. J. Am. Chem. Soc. 1953, 75, 2639-2644. Straus, F. Ber. 1909, 42, 2866-2995.
59. Grovenstein, E.; Lee, D. E. J. Am. Chem. Soc. 1953, 75, 2639-2644. Straus, F. Ber. 1909, 42, 2866-2995.
60. Schlubach, H. H.; Repenning, K. Liebig's Ann. 1958, 614, 37-46.
61. Brown, H. C.; Lane, C. F. Tetrahedron 1988, 44, 2763-2772.
62. Gamet, P. M.; Nagel, D. L.; Reilly, P. J.; Lawson, T.; Sharpe, J.; Toth, B. J. Org. Chem. 1988, 53, 1064-1071.
63. 2
64. Wehrli, R.; Heimgartner, H.; Schmid, H.; Hansen, H.-J. Helv: Chim. Acta 1977, 60, 2034-2061.
65. Fuson, R. C.; Horning, E. C.; Rowland, S. P.; Ward, M. L. In Organic Syntheses; Horning, E. C., Ed.; Wiley: New York, 1955, Collect. Vol. III, pp 549-551.
66. Klages, A. Chem Ber. 1902, 35, 2245-2262.
67. Nightingale, D.; Radford, H. D. J. Org. Chem. 1949, 14, 1089-1093.
68. Vavon, G.; Bolle, J. C. R. Hebd. Seances Acad. Sci. 1937, 204, 1826.
69. Hurd, C. D.; Ensor, E. H. J. Am. Chem. Soc. 1950, 72, 5135-5137.
70. (a) Goerine, H. L.; Kantner, S. S.; Chuna, Chyi J. Org. Chem. 1983, 48, 715-721.
71. (b) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422-426.
72. Doering, W. von E.; Urban, R. S. J. Am. Chem. Soc. 1956, 78, 5938-5942.
73. Mihal, C. P. Am. Ind. Hyg. Assoc. J. 1987, 48, 997-1000.