Importance of substituent intramolecular charge-transfer effect on the molecular conformation of diphenyl ethers

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9794-9800

  Uno, Bunji ^a   Iwamoto, Takuya ^a   Okumura, Noriko ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYL ETHER;

ARTICLE; CONFORMATION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; STRUCTURE ACTIVITY RELATION;

EID: 0032567306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981421q     Document Type: Article

References (49)

1. Uno, B.; Kawakita, T.j'Kano, K.; Ezumi, K.; Kubota, T. Bull. Chem. Soc. Jpn. 1992, 65, 2697.
2. Uno, B.; Kawakita, T.; Kano, K; Okumura, N.; Goto, M.; Kubota, T. Bull. Chem. Soc. Jpn. 1994, 67, 2304.
3. Barakdi, L; Gallinerra, E.; Scoponi, M. Spectrochim. Acta 1987, 43A, 1045.
4. Schaefer, T.; Penner, G. H.; Takeuchi, C.; Tseki, P. Can. J. Chem. 1988, 66, 1647.
5. Kendrick, J. J. Chem. Soc., Faraday Trans. 1990, 86, 3995.
6. Verot, S.; Battes, P. Con. J. Chem. 1995, 73, 581.
7. Dais, P. Magn. Beson. Chem. 1987, 25, 141.
8. Chao, J.; Desando, M. A.; Gourlay, D. L.; On-, D. E.; Waller, S. J. Phys. Chem. 1984, 88, 711.
9. van der Heijiden, S. P. N.; Griffith, E. A. H.; Chandler, W. D.; Robertson, B. E. Can. J. Chem. 1975,53,2084.
10. (b) Gurtu, K.; Chandler, W. D.; Robertson, B. E. Can. J. Chem. 1975,53, 2093.
11. Bergman, J. J.; Griffith, E. A. H.; Chandler, W. D.; Robertson, B. E. Can. J. Chem. 1973, 57, 653.
12. Lehmann, F., P. A. Tetrahedron 1974,30, 719.
13. (b) McEachem B. D. M.; Lehmann, F. P. A. J. Mol. Struct. 1972,11,127.
14. Lehmann, F. P. A.; Shefer, E. Rev. Latinoam. Quim. 1972, 3, 91.
15. Cory, M.; Mckee, D. D.; Kagan, J.; Henry, D. W.; Miller, J. A. J. Am. Chem. Soc. 1985, 707, 2528.
16. Fujikawa, K.; Kondo, K; Yokomichi, L; Kimura, G.; Haga, T.; Nishiyama, R. Agric. Biol. Chem. 1970, 34, 68.
17. Kollman, P. A.; Murray, W. J.; NUSS, M. E.; Horgensen, E. C.; Rothenberg, S. J. Am. Chem. Soc. 1973, 95, 8518.
18. Lehmann F. P. A. J. Med. Chem. 1972, 15, 404.
19. Montaudo, G.; Caccamesa, S.; Finocchiaro, P. J. Am. Chem. Soc. 1971, 93, 4202.
20. (b) Montando, G.; Finocchiaro, P.; Trivellone, E.; Bottino, F.; Maravigna, P. Tetrahedron 1971,27, 2125.
21. Montando, G.; Finocchiaro, P. J. Am. Chem. Soc. 1972, 94, 6745.
22. Montando, G.; Finocchiaro, P.; Caccamesa, S. J. Org. Chem. 1973, 38, 170.
23. (e) Montaudo, G.; Finocchiaro, P. Can. J. Chem. 1974, 52, 767.
24. Weston, P. E.; Adkins, H. J. Am. Chem. Soc. 1928, 50, 859.
25. Factor, A.; Finkbeiner, H.; Terusst, R. A.; White, D. M. J. Org. Chem. 1970, 35, 57.
26. Tomita, M. J. Pharm. Soc. Jpn. 1957, 77, 1024.
27. Uno, B.; Ninomiya, Y.; Kano, K.; Kubota, T. Spectrochim. Acta 1987, 43A, 955.
28. Kubota, T.; Uno, B.; Matsuhisa, Y.; Miyazaki, H.; Kano, K. Chem. Pharm. Bull. 1983, 31, 373.
29. Hehre, W. J.; Radom, L.; Schleyer, P. v. R. Ab Initia Molecular Orbital Theory; John Wiley & Sons: New York, 1986; p 93.
30. Ellis, R. L.; Kuehnlenz, G.; Jaffe, H. H. Theor. Chim. Acta 1972, 26, 131.
31. (b) Kuehnlenz, G.; Jaffe, H. H. J. Chem. Phys. 1973,58, 2238.
32. Tinland, B. Mol. Phys. 1969,16, 413.
33. Lipari, N. O.; Duke, C. B. J. Chem. Phys. 1975,63,1748.
34. (e) Duke, C. B.; Lipara, N. O. J. Chem. Phys. 1975, 63,1758.
35. (f) Jacques, P.; Faure, J.; Achalvet, D.; Jaffe, H. H. J. Phys. Chem. 1981, 85, 473.
36. Malaga, N.; Nishimoto, K. Z. Phys. Chem., N. F. 1957,13,140.
37. Higashi, K.; Uyeo, S. Bull. Chem. Soc. Jpn. 1939, 14, 87, and references cited therein.
38. Jaffé, H. H.; Orchin, M. Theory and Application of Ultraviolet Spectroscopy; Willy Interscience: New York, 1974.
39. Uno, B.; Kubota, T. THEOCHEM 1991, 230, 247.
40. Nagakura, S.; Tanaka, J. J. Chem. Phys. 1954, 22, 236.
41. (b) Nagakura, S. J. Chem. Phys. 1955,23,1441.
42. Tanaka, J.; Nagakura, S. J. Chem. Phys. 1956, 24, 1274.
43. Nagakura, S.; Kojima, M.; Maruyama, Y. J. Mol. Spectrosc. 1964, 13, 174.
44. Kobayashi, T.; Kubota, T.; Ezumi, K. J. Am. Chem. Soc. 1983, 105, 2172.
45. Yamakawa, M.; Kubota, T.; Ezumi, K.; Mizuno, Y. Spectrochim. Acte 1974, 30, 2103.
46. Kimura, K.; Nagakura, S. Mol. Phys. 1965,9,117.
47. (b) Kimura, K.; Tsubomura, H.; Nagakura, S. Bull. Chem. Soc. Jpn. 1964,37,1336.
48. Nagakura, S.; Kimura, K J. Chem. Soc. Jpn., Pure Chem. Sect. 1965, 86, 1.
49. Suzuki, S.; Fujii, T. Bull. Chem. Soc. Jpn. 1975, 48, 835.