Intramolecular CH-π interaction. Substituent effect as a probe for hydrogen bond-like character

Journal of Physical Organic Chemistry

Volumn 13, Issue 10, 2000, Pages 620-623

  Hirota, Minora ^a   Sakaibara, Kazuhisa ^a   Suezawa, Hiroko ^a   Yuzuri, Tomoaki ^a   Ankai, Eikoh ^a   Nishio, Motohiro ^b  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Charge transfer; Hydrogen bond; Intramolecular CH interaction; Substituent effect

Indexed keywords

EID: 0001290339     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-1395(200010)13:10<620::AID-POC262>3.0.CO;2-F     Document Type: Article

References (30)

1. (a) Kodama Y, Nishihata K, Nishio M, Iitaka Y. J. Chem. Soc., Perkin Trans. 2 1976; 1490;;
2. (b) Hirota M, Takahashi Y, Nishio M, Nishihata K. Bull. Chem. Soc. Jpn. 1978; 51: 2358.
3. (a) Nishio M, Hirota M. Tetrahedron 1989; 45: 7201;
4. (b) Nishio M, Umezawa Y, Hirota M, Takeuchi Y. Tetrahedron 1995; 51: 8665;
5. (c) Nishio M, Hirota M, Umezawa Y. The CH/π Interaction - Evidence, Nature and Consequences. Wiley-VCH: Weinheim, 1998.
6. (a) Green RD. Hydrogen Bonding by CH Group. John Wiley & Sons: New York, 1984;
7. (b) Beckman E, Faust O. Z. Phys. Chem. 1914; 89:235: 247.
8. (a) Price SL, Stone AJ. J. Chem. Phys. 1987; 86: 2859;
9. (b) Pawliszyn J, Szezesniak MM, Scheiner S. J. Phys. Chem. 1984; 88: 1726.
10. (a) Hozba P, Selzle HL, Schlag EW. J. Phys. Chem. 1996; 100: 18790;
11. (b) Cubero E, Oronzco M, Hozba P, Luque FJ. J. Phys. Chem. 1999; 103: 6394.
12. Ehama R, Yokoo A, Tsushima M, Yuzuri T, Suezawa H, Hirota M. Bull. Chem. Soc. Jpn. 1993; 66: 814.
13. Coulson CA. In Hydrogen Bonding, Hadzi D, Thompson HW, (eds). Pergamon Press: Oxford, 1959; 339.
14. (a) Morokuma K, Wipff G. Chem. Phys. Lett. 1980; 74: 400;
15. (b) Morokuma K. Acc. Chem. Res. 1977; 10: 294;
16. (c) Takagi T, Tanaka A, Matsuo S, Maezaki H, Tani M, Fujiwara H, Sasaki Y. J. Chem. Soc., Perkin Trans. 2 1987; 1015;
17. (d) Perutz MF. Philos. Trans. R. Soc. London. Ser. A 1993; 345: 105.
18. (a) Abe K, Hirota M, Morokuma K. Bull. Chem. Soc. Jpn. 1985; 58: 2713;
19. (b) Araki S, Sakakibara K, Hirota M, Nishio M, Tsuzuki S, Tanabe K. Tetrahedron Lett. 1991; 6587.
20. (a) Josien ML, Sourisseau G. Bull. Soc. Chim. Fr. 1955; 178;
21. (b) Josien ML, Sourisseau G. Castinel C. Bull. Soc. Chim. Fr. 1955; 1539;
22. (c) Josien ML, Sourisseau G. In Hydrogen Bonding, Hadzi D, Thompson HW, (eds). Pergamon Press: Oxford, 1959, 129;
23. (d) Allerhand A, von P, Schleyer R. J. Am. Chem. Soc. 1963; 85: 1715.
24. (a) Karatsu M, Suezawa H, Abe K, Hirota M, Nishio M. Bull. Chem. Soc: Jpn. 1986; 59: 3529;
25. (b) Hirota M, Abe K. Suezawa H, Nishio M. J. Mol. Struct. 1985; 126: 455.
26. Adcock LJ, Zang H. J. Org. Chem. 1995; 60: 1999.
27. (a) Hammett LP, Chem. Rev. 17: 225;
28. (b) Hammett LP. Physical Organic Chemistry. McGraw-Hill: New York, 1970; 347;
29. (c) Jaffe HH. Chem. Rev. 1953; 53: 191.
30. Suezawa H, Mori A, Sato M, Ehama R, Akai I, Sakakibara K, Hirota M, Nishio M, Kodama Y. J. Phys. Org. Chem. 1993; 6: 399.