Conformation of aromatic rings in isolable atropisomers of 2-arylindoline derivatives and kinetic evidences for π-π interaction

Tetrahedron

Volumn 66, Issue 4, 2010, Pages 898-903

  Eto, Masashi ^a   Yamaguchi, Koki ^b   Shinohara, Itaru ^b   Ito, Fumikazu ^b   Yoshitake, Yasuyuki ^b   Harano, Kazunobu ^b  

^a TOKAI UNIVERSITY   (Japan)

^b SOJO UNIVERSITY   (Japan)

Author keywords

Interaction; 1 Aroyl 2 aryl 3,3 dimethylindoline; Diastereomeric atropisomer; Equilibrium constant; Substituent effect

Indexed keywords

BENZENE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONFORMATION; DIASTEREOISOMER; EQUILIBRIUM CONSTANT; PRIORITY JOURNAL;

EID: 72149100501     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.102     Document Type: Article

References (36)

1. Oki M. Angew. Chem., 88 (1976) 67-74
2. Oki M. In: Allinger N.L., Eliel E.L., and Wilen S.H. (Eds). Topics in Stereochemistry Vol. 14 (1983), John Wiley & Sons, New York, NY 47-79
3. Oki M. Acc. Chem. Res. 23 (1990) 351-356
4. Hunter C.A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1584-1586
5. Hunter C.A. Chem. Soc. Rev. 23 (1994) 101-109
6. Cozzi F., Cinquini M., Annunziata R., Dwyer T., and Siegel J.S. J. Am. Chem. Soc. 114 (1992) 5729-5733
7. Cozzi F., Cinquini M., Annunziata R., and Siegel J.S. J. Am. Chem. Soc., 115 (1993) 5330-5331
8. Harano K., Yasuda M., Ida Y., Komori T., and Taguchi T. Cryst. Struct. Commun. 10 (1981) 165-171
9. Eto M., Harano K., Hisano T., and Kitamura T. J. Heterocycl. Chem., 29 (1992) 311-315
10. Kitamura T., Harano K., and Hisano T. Chem. Pharm. Bull. 40 (1992) 2255-2261
11. Eto M., Ito F., Kitamura T., and Harano K. Heterocycles 38 (1994) 2159-2163
12. Eto M., Ito F., Kitamura T., and Harano K. Heterocycles 43 (1996) 1159-1163
13. Watanabe A., Moriguchi M., Ito I., Yoshitake Y., Eto M., and Harano K. Heterocycles 53 (2000) 1-6
14. Ito F., Moriguchi T., Yoshitake Y., Eto M., Yahara S., and Harano K. Chem. Pharm. Bull. 51 (2003) 688-696
15. Watanabe A., Yamaguchi K., Ito F., Yoshitake Y., and Harano K. Heterocycles 71 (2007) 343-359
16. Eto M., Ito F., Sato H., Shinohara I., Yamaguchi K., Yoshitake Y., and Harano K. Heterocycles 78 (2009) 1485-1496
17. Nishio M., Hirota M., and Umezawa Y. The CH⋯π interaction; Evidence Nature and Consequences (1998), Wiley, New York, NY
18. Taylor R., and Kennard O. J. Am. Chem. Soc., 104 (1982) 5063-5070
19. Desiraju G.R. Acc. Chem. Res. 24 (1991) 290-296
20. Steiner T., Kanters J.A., and Kroon J.A. Chem. Commun. (1996) 1277-1278
21. Steiner T. Crystallogr. Rev. 6 (1996) 1-57
22. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian,, Wallingford CT
23. MOPAC2009:. Stewart J.J.P. Stewart computational chemistry, version 9.062M web. Http://OpenMOPAC.net
24. The PM6 calculation reproduced the relative stability of the isomers. The heat of formations of ground-state structures for syn (4a) and anti (5a) are -5.9 and -8.0 kcal/mol, respectively (see Table 2).
25. 6. On the other hand, the protons of the anti isomers (5a-f) appeared characteristically as sharp singlets at 9.5-9.8 ppm under the same conditions of measurement. The difference in the signal shape suggests that the decrease of conformational mobility of the hydroxyaryl group due to the intramolecular ArOH⋯N interaction.{A figure is presented}
26. Hammet L.P. Physical Organic Chemistry. 2nd ed. (1970), McGraw-Hill, New York, NY
27. Henri-Rousseau O., and Texier F. J. Chem. Educ. 55 (1978) 437-440
28. Sustmann R., and Trill H. Angew. Chem., Int. Ed. Engl. 11 (1972) 838-840
29. Klamt A., and Schurmann G. J. Chem. Soc., Perkin Trans. 2 (1993) 799-805
30. Klamt A. J. Phys. Chem. 100 (1996) 3349-3353
31. 5c The activation energies of 4b and the 2-methoxynaphthyl derivative (6b) in diphenylether are 24.2 and 20.3 kcal/mol, respectively. The barrier to rotation of 6b is lower than that of 4b. This fact suggests that the intramolecular ArOH⋯N interaction partially affects the stabilization of the rotamers.
32. SIR92:. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M., Polidori G., and Camalli M. J. Appl. Crystallogr. 27 (1994) 435-436
33. CrystalStructure 3.6.0:. Crystal Structure Analysis Package (2000-2004), Rigaku and Rigaku/MSC, USA
34. CRYSTALS Issue 10:. Watkin D.J., Prout C.K., Carruthers J.R., and Betteridge P.W. Chemical Crystallography Laboratory (1996), Oxford, UK
35. Senda N. Idemitsu Technical Report 49 (2006) 106-111
36. Scott A.P., and Radom L. J. Phys. Chem. 100 (1996) 10502-10513