Synthesis of Two Bis-m-quinomethanes. An Experimental Study of Connectivity Effects on the Equal-Parity Criterion for Low-Spin Ground States in Alternant Non-Kekulé Molecules

Journal of the American Chemical Society

Volumn 108, Issue 6, 1986, Pages 1251-1265

  Seeger, David E ^a   Lahti, Paul M ^a   Berson, Jerome A ^a   Rossi, Angelo R ^b  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845374319     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00266a021     Document Type: Article

References (71)

1. Hückel, E. Z. Phys. Chem., Abt. B 1936, 34, 339.
2. Hund, F. “Linienspektren und periodisches System der Elemente”; Springer-Verlag: Berlin, 1927; p 124.
3. Hund, F. Z. Phys. 1928, 51, 759.
4. Mulliken, R. S. Phys. Rev. 1928, 32, 186.
5. Müller, E.; Bunge, W. Ber. 1936, 69, 2168.
6. Longuet-Higgins, H. C. J. Chem. Phys. 1950, 18, 265.
7. Schlenk, W.; Brauns, M. Ber. 1915, 48, 661, 716.
8. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587.
9. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 497.
10. Misurkin, I. A.; Ovchinnikov, A. A. Russ. Chem. Rev. (Engl. Transl.) 1977, 46, 967.
11. Klein, D. J. Pure Appl. Chem. 1983, 55, 299.
12. Klein, D. J.; Nelin, C. J.; Alexander, S.; Matsen, F. A. J. Chem. Phys. 1982, 77, 3101.
13. Said, M.; Maynau, D.; Malrieu, J.-P.; Garcia Bach, M.-A. J. Am. Chem. Soc. 1984, 106, 571.
14. Dohnert, D.; Koutecky, J. J. Am. Chem. Soc. 1980, 102, 1789.
15. Buenker, R. J.; Peyerimhoff, S. D. J. Chem. Phys. 1968, 48, 354.
16. Kollmar, H.; Staemmler, V. Theor. Chim. Acta 1978, 48, 223.
17. Borden, W. T.; Davidson, E. R.; Hart, P. J. Am. Chem. Soc. 1978, 100, 388.
18. Masamune, S.; Souto-Bachiller, F. A.; Machiguchi, T.; Bertie, J. E. J. Am. Chem. Soc. 1978, 100, 4889.
19. Whitman, D. W.; Carpenter, B. K. J. Am. Chem. Soc. 1980, 102, 4272.
20. Dowd, P. J. Am. Chem. Soc. 1970, 92, 1066.
21. Dixon, D. A.; Foster, R.; Halgren, T.; Lipscomb, W. N. J. Am. Chem. Soc. 1978, 100, 1359.
22. Gajewski, J. J. “Hydrocarbon Thermal Isomerizations”; Academic Press: New York, 1981; pp 138–155.
23. Roth, W. R.; Erker, W. Angew. Chem., Intl. Ed. Engl. 1973, 12, 503.
24. Grimme, W.; Rother, H. J. Angew. Chem., Intl. Ed. Engl. 1973, 12, 502.
25. Bauld, N. L.; Chang, C.-S. J. Am. Chem. Soc. 1972, 94, 7594.
26. Roth, W. R.; Scholz, B. P. Chem. Ber. 1982, 115, 1197.
27. Seeger, D. E.; Berson, J. A. J. Am. Chem. Soc. 1983, 105, 5144, 5146.
28. Lahti, P. M.; Rossi, A. R.; Berson, J. A. J. Am. Chem. Soc. 1985, 107, 2273.
29. Rule, M.; Matlin, A. R.; Dougherty, D. A.; Hilinski, E. F.; Berson, J. A. J. Am. Chem. Soc. 1979, 101, 5098.
30. Seeger, D. E.; Hilinski, E. F.; Berson, J. A. J. Am. Chem. Soc. 1981, 103, 720.
31. Rule, M.; Matlin, A. R.; Seeger, D. E.; Hilinski, E. F.; Dougherty, D. A.; Berson, J. A. Tetrahedron 1982, 38, 787.
32. Matlin, A. R.; Inglin, T. A.; Berson, J. A. J. Am. Chem. Soc. 1982, 104, 4954.
33. Platz, M. S.; Burns, J. R. J. Am. Chem. Soc. 1979, 101, 4425.
34. Arnold, R. T.; Rondestvedt, E. J. Am. Chem. Soc. 1945, 67, 1265.
35. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.
36. Wasserman, E.; Hutton, R. S. Acc. Chem. Res. 1977, 10, 27 and references cited therein.
37. Wertz, J. E.; Bolton, J. R. “Electron Spin Resonance: Elementary Theory and Practical Applications”; McGraw Hill: New York, 1967.
38. Weltner, W., Jr. “Magnetic Atoms and Molecules”; Scientific and Academic Editions: New York, 1983.
39. Huber, R.; Schwoerer, M. Chem. Phys. Lett. 1980, 72, 10.
40. Schwoerer, M.; Huber, R. A.; Hartl, W. Chem. Phys. 1981, 55, 97.
41. Wasserman, E.; Murray, R. W.; Yager, W. A.; Trozzolo, A. M.; Smolinsky, G. J. Am. Chem. Soc. 1967, 89, 5076.
42. Abragam, A.; Bleaney, B. “Electron Paramagnetic Resonance of Transition Ions”; Oxford University Press: Oxford, England, 1970.
43. Huber, R. Ph.D. Thesis, Universitat Bayreuth, 1981, as cited in ref 21.
44. Reference 20a, Appendix B, especially pp 427–434.
45. Dowsing, R. D. J. Magn. Reson. 1970, 2, 332.
46. Benk, H.; Sixl, H. Mol. Phys. 1981, 42, 779.
47. Higuchi, J. J. Chem. Phys. 1963, 38, 1237.
48. Higuchi, J. 1964, 39, 1847.
49. Fessenden, R. W.; Schuler, R. H. J. Chem. Phys. 1963, 39, 2147.
50. Muller, J.-F.; Muller, D.; Dewey, H. J.; Michl, J. J. Am. Chem. Soc. 1978, 100, 1629.
51. Gisin, M.; Rommel, E.; Wirz, J.; Burnett, M. N.; Pagni, R. M. J. Am. Chem. Soc. 1979, 101, 2216.
52. Gisin, M.; Wirz, J. Helv. Chim. Acta 1983, 66, 1556.
53. Goodman, J. L.; Peters, K. S.; Lahti, P. M.; Berson, J. A. J. Am. Chem. Soc. 1985, 107, 276.
54. Breslow, R.; Chang, H. W.; Hill, R.; Wasserman, E. J. Am. Chem. Soc. 1967, 89, 1112.
55. Closs, G. L.; Doubleday, C. E. J. Am. Chem. Soc. 1972, 94, 9248; 1973, 95, 2735.
56. Kalo, S.; Morokuma, K.; Feller, D.; Davidson, E. R.; Borden, W. T. J. Am. Chem. Soc. 1983, 105, 1791.
57. Borden, W. T. “Diradicals”, Academic Press: New York, 1982; Chapter 1 and references cited therein.
58. Dixon, D. A.; Dunning, T. H., Jr.; Eades, R. A.; Kleier, D. A. J. Am. Chem. Soc. 1981, 103, 2878.
59. Lahti, P. M., Ph.D. Thesis, Yale University, 1985
60. Appendix A. Lahti, P. M.; Rossi, A. R.; Berson, J. A. J. Am. Chem. Soc. 1985, 107, 4362.
61. Du, P.; Hrovat, D.; Borden, W. T.; Lahti, P. M.; Rossi, A. R.; Berson, J. A., submitted for publication.
62. Schimelpfenig, C. W. J. Org. Chem. 1975, 40, 1493.
63. Wasserman, H. H.; Doumaux, A. R., Jr. J. Am. Chem. Soc. 1962, 84, 4611.
64. Katz, T. J.; Balogh, V.; Schulman, J. J. Am. Chem. Soc. 1968, 90, 735.
65. Baldwin, J. E.; Pudussery, R. G. Chem. Commun. 1968, 408.
66. Seeger, D. E. Ph.D. Dissertation, Yale University, 1983, p 166.
67. Lahti, P. M. Ph.D. Dissertation, Yale University, 1985, p 369.
68. Ridley, J.; Zerner, M. Theor. Chim. Acta 1973, 32, 11.
69. Ridley, J.; Zerner, M. Theor. Chim. Acta 1976, 42, 233.
70. Platz, M. S.; Berson, J. A. J. Am. Chem. Soc. 1980, 102, 2358.
71. Carrington, A.; McLachlan, A. D. “Introduction to Magnetic Resonance”; Harper and Row: New York, 1967; p 5.