Attractive interaction caused by the linear F···Se-C alignment in naphthalene peri positions

Journal of the American Chemical Society

Volumn 120, Issue 15, 1998, Pages 3635-3640

  Nakanishi, Warô ^a   Hayashi, Satoko ^a   Sakaue, Akira ^a   Ono, Go ^a   Kawada, Yuzo ^b  

^a WAKAYAMA UNIVERSITY   (Japan)

^b IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IRON; NAPHTHALENE DERIVATIVE; SELENIUM;

ARTICLE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0032557203     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974070q     Document Type: Article

References (49)

1. (a) Glass, R. S.; Andruski, S. W.; Broeker, J. L. Rev. Heteroatom Chem. 1988, 1, 31. Glass, R. S.; Andruski, S. W.; Broeker, J. L.; Firouzabadi, H.; Steffen, L. K.; Wilson, G. S. J. Am. Chem. Soc. 1989, 111, 4036. Glass, R. S.; Adamowicz, L.; Broeker, J. L. J. Am. Chem. Soc. 1991, 113, 1065.
2. (a) Glass, R. S.; Andruski, S. W.; Broeker, J. L. Rev. Heteroatom Chem. 1988, 1, 31. Glass, R. S.; Andruski, S. W.; Broeker, J. L.; Firouzabadi, H.; Steffen, L. K.; Wilson, G. S. J. Am. Chem. Soc. 1989, 111, 4036. Glass, R. S.; Adamowicz, L.; Broeker, J. L. J. Am. Chem. Soc. 1991, 113, 1065.
3. (a) Glass, R. S.; Andruski, S. W.; Broeker, J. L. Rev. Heteroatom Chem. 1988, 1, 31. Glass, R. S.; Andruski, S. W.; Broeker, J. L.; Firouzabadi, H.; Steffen, L. K.; Wilson, G. S. J. Am. Chem. Soc. 1989, 111, 4036. Glass, R. S.; Adamowicz, L.; Broeker, J. L. J. Am. Chem. Soc. 1991, 113, 1065.
4. (b) Fujihara, H.; Ishitani, H.; Takaguchi, Y.; Furukawa, N. Chem. Lett. 1995, 571.
5. (c) Fujihara, H.; Yabe, M.; Chiu, J.-J.; Furukawa, N. Tetrahedron Lett. 1991, 32, 4345. Furukawa, N.; Fujii, T.; Kimura, T.; Fujihara, H. Chem. Lett. 1994, 1007.
6. (c) Fujihara, H.; Yabe, M.; Chiu, J.-J.; Furukawa, N. Tetrahedron Lett. 1991, 32, 4345. Furukawa, N.; Fujii, T.; Kimura, T.; Fujihara, H. Chem. Lett. 1994, 1007.
7. (d) Fujihara, H.; Saito, R.; Yabe, M.; Furukawa, N. Chem. Lett. 1992, 1437.
8. (e) Nakanishi, W. Chem. Lett. 1993, 2121.
9. (f) Nakanishi, W.; Hayashi, S.; Toyota, S. J. Chem. Soc., Chem. Commun. 1996, 371.
10. (g) Nakanishi, W.; Hayashi, S.; Yamaguchi, H. Chem. Lett. 1996, 947.
11. (a) Mallory, F. B. J. Am. Chem. Soc. 1973, 95, 7747.
12. (b) Mallory, F. B.; Mallory, C. W.; Fedarko, M.-C. J. Am. Chem. Soc. 1974, 96, 3536.
13. (c) Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Am. Chem. Soc. 1975, 97, 4770. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457. Mallory, F. B.; Mallory, C. W.; Baker, M. B. J. Am. Chem. Soc. 1990, 112, 2577.
14. (c) Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Am. Chem. Soc. 1975, 97, 4770. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457. Mallory, F. B.; Mallory, C. W.; Baker, M. B. J. Am. Chem. Soc. 1990, 112, 2577.
15. (c) Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Am. Chem. Soc. 1975, 97, 4770. Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457. Mallory, F. B.; Mallory, C. W.; Baker, M. B. J. Am. Chem. Soc. 1990, 112, 2577.
16. (d) Ernst, L.; Ibrom, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1881. Ernst, L.; Ibrom, K.; Marat, K.; Mitchell, R. H.; Bodwell, G. J.; Bushnell, G. W. Chem. Ber. 1994, 127, 1119.
17. (d) Ernst, L.; Ibrom, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1881. Ernst, L.; Ibrom, K.; Marat, K.; Mitchell, R. H.; Bodwell, G. J.; Bushnell, G. W. Chem. Ber. 1994, 127, 1119.
18. Mallory, F. B.; Luzik, E. D., Jr.; Mallory, C. W.; Carroll, P. J. J. Org. Chem. 1992, 57, 366. Mallory, F. B.; Mallory, C. W. J. Am. Chem. Soc. 1985, 107, 4816.
19. Mallory, F. B.; Luzik, E. D., Jr.; Mallory, C. W.; Carroll, P. J. J. Org. Chem. 1992, 57, 366. Mallory, F. B.; Mallory, C. W. J. Am. Chem. Soc. 1985, 107, 4816.
20. Johannsen, I.; Eggert, H. J. Am. Chem. Soc. 1984, 106, 1240. Johannsen, I.; Eggert, H.; Gronowitz, S.; Hörnfeldt, A.-B. Chem. Scr. 1987, 27, 359. Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1992, 114, 3117.
21. Johannsen, I.; Eggert, H. J. Am. Chem. Soc. 1984, 106, 1240. Johannsen, I.; Eggert, H.; Gronowitz, S.; Hörnfeldt, A.-B. Chem. Scr. 1987, 27, 359. Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1992, 114, 3117.
22. Johannsen, I.; Eggert, H. J. Am. Chem. Soc. 1984, 106, 1240. Johannsen, I.; Eggert, H.; Gronowitz, S.; Hörnfeldt, A.-B. Chem. Scr. 1987, 27, 359. Fujihara, H.; Mima, H.; Erata, T.; Furukawa, N. J. Am. Chem. Soc. 1992, 114, 3117.
23. (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265.
24. (b) Barton, D. H. R.; Hall, M. B.; Lin, Z.; Parekh, S. I.; Reibenspies, J. J. Am. Chem. Soc. 1993, 115, 5056.
25. 77Se chemical shifts of 1, 2, 3, and 4 were δ 440.9, 250.4, 354.2, and 159.0, respectively.
26. Although the discussion is focused on structure A, it is also valid on structure B.
27. Pauling, L. The Nature of the Chemical Bond. 3rd ed.; Cornell University Press: Ithaca, New York, 1960; Chapter 7. See also; Bondi, A. J. Phys. Chem. 1964. 68, 441.
28. Pauling, L. The Nature of the Chemical Bond. 3rd ed.; Cornell University Press: Ithaca, New York, 1960; Chapter 7. See also; Bondi, A. J. Phys. Chem. 1964. 68, 441.
29. Rosenfield, R. E., Jr.; Parthasarathy, R.; Dunitz, J. D. J. Am. Chem. Soc. 1977, 99, 4860.
30. Ramasubbu, N.; Parthasarathy, R. Phosphorus Sulfur 1987, 31, 221.
31. Gaussian 94, Revision D.4; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
32. 1 = 180°.
33. 2Se. The results exhibit that the adduct is destabilized relative to the free components. The fluoro and selanyl groups cannot exist this close if the two groups are not joined by the naphthalene 1,8-positions.
34. MacSpartan Plus Ver. 1.0, Hehre, H. J. Wavefunction, Inc.
35. 1 = 180.0° and the corresponding molecules were essentially the same as those exhibited in Figure 3.
36. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054.
37. NBO Version 3.1; Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; Gaussian Link 607.
38. (a) Pimentel, G. C. J. Chem. Phys. 1951, 19, 446. Musher, J. I. Angew. Chem., Int. Ed. Engl. 1969, 8, 54.
39. (a) Pimentel, G. C. J. Chem. Phys. 1951, 19, 446. Musher, J. I. Angew. Chem., Int. Ed. Engl. 1969, 8, 54.
40. (b) Chen, M. M. L.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1647.
41. (c) Cahill, P. A.; Dykstra, C. E.; Martin, J. C. J. Am. Chem. Soc. 1985, 107, 6359. See also: Hayes, R. A.; Martin, J. C. Sulfurane Chemistry In Organic Sulfur Chemistry: Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., A., Eds.; Elsevier: Amsterdam, 1985; Chapter 8.
42. (c) Cahill, P. A.; Dykstra, C. E.; Martin, J. C. J. Am. Chem. Soc. 1985, 107, 6359. See also: Hayes, R. A.; Martin, J. C. Sulfurane Chemistry In Organic Sulfur Chemistry: Theoretical and Experimental Advances; Bernardi, F., Csizmadia, I. G., Mangini, A., A., Eds.; Elsevier: Amsterdam, 1985; Chapter 8.
43. Nakanishi, W.; Hayashi, S.; Toyota, S. Unpublished results.
44. We have encountered a facile reductive C-F bond cleavage in the reaction of sodium 8-fluoro-1-naphthaleneselenate with p-(methoxybenzene)diazonium chloride, which yields not 1 but 3. The C-F bond cleavage must be, we believe, the reflection of the nonbonded interaction between F and Se atoms.
45. Adcock, W.; Matthews, D. G.; Rizvi, S. Q. A. Aust. J. Chem. 1971, 24, 1829.
46. 21 The observed value for carbon was ca. 1% larger than that of the calculated one while that for hydrogen was satisfactory.
47. 20 is in progress, and the results will be reported elsewhere.
48. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, A46, 467.
49. Sakurai, T.; Kobayashi, K. Rep. Inst. Phys. Chem. Res. 1979, 55, 69.