Does π-σ-π through-bond coupling significantly increase C - C bond lengths?

Journal of the American Chemical Society

Volumn 119, Issue 30, 1997, Pages 7048-7054

  Baldridge, Kim K ^b   Battersby, Thomas R ^a   VernonClark, Russell ^a   Siegel, Jay S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBON;

ARTICLE; CORRELATION FUNCTION; COVALENT BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION;

EID: 0030847093     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9622315     Document Type: Article

References (68)

1. Allen, F.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J Chem. Soc., Perkin Trans 2 1987, SI.
2. Pauling, L. Nature of the Chemical Bond; 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
3. Hoffmann, R. Acc: Chem. Res. 1971, 4, 1.
4. Gleiter, R. Angew. Chem., Int. Ed. Engl. 1974, 13, 696.
5. Dougherty, D. A.; Hounshell, W. D.; Schlegel, H. B.; Bell, R. A.; Mislow, K. Tetrahedron Lett. 1976, 39, 3479.
6. Dougherty, D. A.; Schlegel, H. B.; Mislow, K. Tetrahedron 1978, 34, 1441.
7. Osawa, E.; Ivanov, P. M.; Jaime, C. J. Org. Chem. 1983, 48, 3990.
8. Osawa, E., Kanematsu, K., Osawa, E., Kanematsu, K., Eds.; Verlag Chemie International: Deerfield Beach, FL, 1986; Chapter 7.
9. Harano, K.; Ban, T.; Yasuda, M.; Osawa, E.; Kanematsu, K. J. Am. Chem. Soc. 1981, 103, 2310.
10. Okamoto, Y.; Harano, K.; Yasuda, M.; Osawa, E.; Kanematsu, K. Chem. Pharm. Bull. 1983, 31, 2526.
11. Dougherty, D. A.; Choi, C. S.; Kaupp, G.; Buda, A. B.; Rudzin'ski, J. M.; Osawa, E. J. Chem. Soc. Perkin Trans. 2 1986, 1063-70.
12. Battersby, T. R.; Gantzel, P.; Baldridge, K. K.; Siegel, J. S. Tetrahedron Lett. 1995, 36, 845-848.
13. Bischof, J. A.; Hashmall, E.; Heilbronner, E.; Hornung, V. Tetrahedron Lett. 1969, 46, 4025.
14. Heilbronner, E.; Muszkat, K. A. Chem. Phys. Lett. 1972, 13, 301.
15. Muszkat, K. A.; Schäublin, J. Chem. Phys. Lett. 1972, 13, 301.
16. Kovac, B.; Mohraz, M.; Heilbronner, E.; Boekelheide, V.; Hopf, H. J. Am. Chem. Soc. 1980, 102, 4314.
17. Kovac, B.; Allan, M.; Heilbronner, E. Helv. Chim. Acta 1981, 64, 430.
18. Gleiter, R.; Eckert-Maksie, M.; Schäfer, W.; Truesdale, E. A. Chem. Ber. 1982, 115, 2009.
19. Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, 1988; pp 115-194.
20. Balaji, V.; Ng, L.; Jordan, K. D.; Paddon-Row, M. N.; Patney, H. K. J. Am. Chem. Soc. 1987, 109, 6957.
21. Beratan, D. N.; Onuchic, J. J.; Winkler, J. R.; Gray, H. B. Science 1992, 258, 1740.
22. Paddon-Row, M. N.; Patney, H. K.; Brown, R. S.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 5575-77.
23. Paddon-Row, M. N. Ace. Chem. Res. 1982, 15, 245-51.
24. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Jensen, J. H.; Koseki, S.; Gordon, M. S.; Nguyen, K. A.; Windus, T. L.; Albert, S. T. QCPE Bull. 1990, 10.
25. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Elbert, S. T. J. Comput. Chem. 1993, 14, 1347.
26. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039.
27. Dunning, T. H., Jr.; Hay, P. J. Modem Theoretical Chemistry; Plenum: New York, 1976.
28. Dunning, T. H. J. Chem. Phys. 1971, 55, 716-723.
29. Koopmans, T. Physica 1934, 1, 104.
30. Niessen, V.; Cederbaum, L. S.; Kraemer, W. P. J. Chem. Phys. 1976, 65, 1378.
31. Schulman, J. M.; Moskowitz, J. W. J. Chem. Phys. 1967, 47, 3491.
32. Almlof, J.; Roos, B.; Wahlgren, U.; Johansen, H. J. Electron Spectrosc. Relat. Phenom. 1973, 2, 51-74.
33. Jordan, K. D.; Paddon-Row, M. N. J. Phys. Chem. 1992, 96, 1188-1196.
34. Harada, J.; Ogawa, K.; Tomoda, S. J. Am. Chem. Soc. 1995, 117, 4476.
35. Kahr, B.; Mitchell, C. A.; Chance, J. M.; Vernonclark, R.; Gantzel, P.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1995, 117, 4479-4482.
36. Brundle, C. R.; Robin, M. B.; Kuebler, N. A. J. Am. Chem. Soc. 1971, 94, 1466.
37. Brundle, C. R.; Robin, M. B.; Kuebler, N. A.; Basch, H. J Am. Chem. Soc. 1972, 94, 1451.
38. Narayan, B.; Murrell, J. N. Mol Phys. 1970, 19, 169.
39. Heilbronner, E.; Maier, J. P. Helv. Chim. Acta 1974, 57, 151.
40. Hope, H.; Bernstein, J.; Trueblood, K. N. Acta Crystallogr. 1972, B28, 1733.
41. Brown, D. E.; Beagley, B. J. Mol. Struct. 1977, 38, 167.
42. Meier, R. J. J. Mol. Struct. 1988, 181, 81.
43. VernonClark, R., University of California, San Diego, 1993.
44. VernonClark, R.; Siegel, J. S. Manuscript in preparation.
45. Lofthagen, M.; VernonClark, R.; Baldridge, K. K.; Siegel, J. S. J. Org. Chem. 1992, 57, 61-9.
46. Battersby, T. Ph.D. Dissertation, University of California, San Diego, 1996.
47. Peters, N. J. Ph. D. Dissertation, University of Illinois, Champaign-Urbana, 1980.
48. Significant changes in bond length were observered only after substituting anions directly on the bicyclohexane framework.
49. Camerman, N.; Camerman, A. J. Am. Chem. Soc. 1970, 92, 2523.
50. Gleiter, R.; Heilbronner, E.; Hekman, M.; Martin, H.-D. Chem. Ber. 1973, 106, 28.
51. Moriarty,. R. M.; Romain, C. R.; Karle, I. L.; Karle, J. J. Am. Chem. Soc. 1965, 87, 3252.
52. Ehrenberg, M. Acta Crystallogr. 1966, 20, 182.
53. Gaultier, J.; Hauw, C.; Boas-Laruent, H. Acta Crystallogr. 1976, B32, 1220.
54. Rüchardt, C.; Beckhaus, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 529.
55. Rüchardt, C.; Beckhaus, H. Top. Curr. Chem. 1986, 130, 1.
56. 59-62 Recently, Leutweiler has found that the "normal" vdW surface for arenes should be extended in the direction perpendicular to the plane of the ring: Leutwieler, S. Private communication. Irngartinger has also studied the anisotropic distribution of electron density in π systems; see: Irngartinger, H. Electron Distribution in the Chemical Bond; Plenum Press: New York, 1982.
57. Bondi, A. J. Phys. Chem. 1964, 68, 441.
58. Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729.
59. Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330.
60. Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-9.
61. Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733.
62. Sharma, C. V. K.; Paneerselvam, K.; Shimoni, L.; Katz, H.; Carrell, H. L.; Desiradju, G. R. Chem. Mater. 1994, 6, 1282.
63. PCMODEL, 5.0 ed.; Serena Sofware: Bloomington, 1993.
64. "By itself E has no physical meaning. In addition, the component terms ... will change depending on their functional forms and choice of parameters." (p 269); "Thus, the values of individual terms, such as stretching, or torsion, etc., have no absolute meaning." (p 273) Boyd, D. B.; Lipkowitz, K. B. J. Chem. Educ. 1982, 59, 269-274.
65. Allinger and Katzenellenbogen have found that inclusion of a new term in the MM3 force field allows them to pick up subtle variations in benzylic bond lengths. The improvement in fit is clear, although proof of hyperconjugation as the mechanism remains in our minds unsubstantiated; see: Allinger, N. L.; Chen, K.; Katzenellenbogen, J. A.; Wilson, S. R.; Anstead, G. M. J. Comput. Chem. 1996, 17, 747.
66. For a related example of force fields underestimating π-πthrough-space distances, see: (a) Ermer, O. Aspekte von Kraftfeldrechnungen; Wolfgang Bauer Verlag: München, 1981. (b) Ermer, O.; Bödecker, C.-D.; Freut, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 55.
67. For a related example of force fields underestimating π-πthrough-space distances, see: (a) Ermer, O. Aspekte von Kraftfeldrechnungen; Wolfgang Bauer Verlag: München, 1981. (b) Ermer, O.; Bödecker, C.-D.; Freut, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 55.
68. Maslak, P.; Kula, J. Mol. Cryst. Liq. Cryst. 1991, 194,293.