X-ray structures of a pair of atropisomers of 1-acyl-2-arylindolines. Remarkable through-space aryl-aryl interaction

Heterocycles

Volumn 43, Issue 6, 1996, Pages 1159-1163

  Eto, Masashi ^a   Ito, Fumikazu ^a   Kitamura, Takeo ^b   Harano, Kazunobu ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b DAIICHI UNIVERSITY OF PHARMACY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742519101     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7430     Document Type: Article

References (15)

1. a) M. Oki, "Topics in Stereochemistry," Vol. 14, ed by N. L. Allinger, E. L. Eliel, and S. H. Wilen, John Wiley and Sons, Inc., New York, 1983, pp. 47-79.
2. b) M. Oki, Angew. Chem., Int. Ed. Engl., 1976, 15, 87.
3. c) M. Oki, Acc. Chem. Res., 1990, 23, 351.
4. d) M. Nakamura and M. Oki, Chem. Lett., 1976, 651
5. W. C. Randall, P. S. Anderson, E. L. Cresson, C. A. Hunt, T. F. Lyon, K. E. Rittle, D. C. Remy, J. P. Springer, J. M. Hirshfield, K. Hoogsteen, M. Williams, E. A. Risley, and J. A. Tataro, J. Med. Chem., 1979, 22, 1222.
6. a) F. Cozzi, M. Cinquini, R. Annunziata, T. Dwyer, and J. S. Siegel, J. Am. Chem. Soc., 1992, 114, 5729.
7. b) F. Cozzi, M. Cinquini, R. Annunziata, and J. S. Siegel, J. Am. Chem. Soc., 1993, 115, 5330.
8. a) Th e X-ray analyses of the 2-(2″,3″-dimethylindolyl)-3,3-dimethylindoline derivatives: K. Harano, M. Yasuda, Y. Ida, T. Komori, and T. Taguchi, Cryst. Struc. Commun., 1981, 10, 165.
9. b) Th e X-ray analyses of 2-(2″-hydroxynaphthyl)-3,3-dimethylindoline derivatives: M. Eto, K. Harano, T. Hisano, and T. Kitamura, J. Heterocycl Chem., 1992, 29, 311.
10. c) T. Kitamura, K. Harano, and T. Hisano, Chem. Pharm. Bull., 1992, 40, 2255
11. f=0.083. The details of the X-ray and MO calculation data will be appeared in a separate paper. The atomic coordinates at the present stage are available by E-mail.
12. a) An average of the values of independent molecules (A, θ=28.7°; B, θ=29.7°). b) An average: Molecule A, 2.970Å; molecul B, 3.000Å. c) An average: Molecule A, 4.692Å; molecule B, 4.952Å.
13. J. J. P. Stewart, QCPE Bull., 1989, 9, 10, idem, J. Comp. Chem., 1989, 10, 209, 221. The MO calculations were performed on a Fujitsu S-4/2 EWS using MOPAC V6.01.
14. J. J. P. Stewart, QCPE Bull., 1989, 9, 10, idem, J. Comp. Chem., 1989, 10, 209, 221. The MO calculations were performed on a Fujitsu S-4/2 EWS using MOPAC V6.01.
15. The AM1 MO calculation on 3b indicated that the HOMO and LUMO are almost entirely localized on the anilino and the nitrobenzoyl moieties, respectively, whereas the NHOMO is localized on the naphtyl moiety. The observed conformation is considered to be very favorble for the HOMO-LUMO interaction of both aryl rings.