CH/π interaction between benzene and model neutral organic molecules bearing acid CH groups

New Journal of Chemistry

Volumn 26, Issue 12, 2002, Pages 1718-1723

  Ugozzoli, Franco ^a   Arduini, Arturo ^a   Massera, Chiara ^a   Pochini, Andrea ^a   Secchi, Andrea ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BASE; BENZENE; CARBON; HYDROGEN; LEWIS ACID; ORGANIC COMPOUND;

AB INITIO CALCULATION; ACIDITY; ARTICLE; BINDING AFFINITY; CORRELATION ANALYSIS; ELECTRON TRANSPORT; GEOMETRY; MOLECULAR INTERACTION; PREDICTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY;

EID: 0036444484     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208432e     Document Type: Article

References (40)

1. (a) M. Nishio, M. Hirota and Y. Umezawa, The CH/π Interaction, Wiley-VCH, New York, 1998;
2. (b) O. Takahashi, Y. Kohno, S. Iwasaki, K. Saito, M. Iwaoka, S. Tomoda, Y. Umezawa, S. Tsuboyama and M. Nishio, Bull. Chem. Soc. Jpn., 2001, 74, 2421;
3. (c) O. Takahashi, S. Tsuboyama, Y. Umezawa, K. Honda and M. Nishio, Tetrahedron, 2000, 56, 6185;
4. (d) Y. Umezawa, S. Tsuboyama, H. Takahashi, J. Uzawa and M. Nishio, Bioorg. Med. Chem., 1999, 7, 2021;
5. (e) R. E. Grillard, F. M. Raymo and J. F. Stoddart, Chem. Eur. J., 1997, 3, 1933;
6. (f) P. Timmermann, W. Verboom and D. N. Reinhoudt, Tetrahedron, 1996, 52, 2663;
7. For a comprehensive literature list see http://www.tim.hi-ho.ne.jp/dionisio/.
8. Y. Iitaka, Y. Kodama, K. Nishihata and M. Nishio, J. Chem. Soc., Chem. Commun., 1974, 389.
9. Y. Kodama, K. Nishihata, M. Nishio and Y. Iitaka, J. Chem. Soc., Perkin Trans. 2, 1976, 1490.
10. Y. Kodama, S. Zushi, K. Nishihata, M. Nishio and J. Uzawa, J. Chem. Soc., Perkin Trans. 2, 1980, 1306.
11. M. Hirota, T. Sekiya, K. Abe, H. Tashiro, M. Karatsu, M. Nishio and E. Osawa, Tetrahedron, 1983, 39, 3091.
12. Y. Nakai, G. Yamamoto, M. Oki, Chem. Lett., 1987, 89.
13. Y. Umezawa, S. Tsuboyama, H. Takahashi, J. Uzawa and M. Nishio, Tetrahedron, 1999, 55, 10047.
14. F. A. Quiocho and N. K. Vyas, Nature, 1984, 310, 381.
15. N. K. Vyas, M. N. Vyas and F. A. Quiocho, Nature, 1987, 327, 635.
16. N. K. Vyas, M. N. Vyas and F. A. Quiocho, Science, 1988, 242, 1290.
17. G. D. Andreetti, A. Pochini and R. Ungaro, J. Chem. Soc., Chem. Commun., 1979, 1005.
18. G. D. Andreetti, O. Ori, F. Ugozzoli, C. Alfieri, A. Pochini and R. Ungaro, J. Inclusion Phenom., 1988, 6, 523.
19. E. Dalcanale, P. Soncini, G. Bacchilega and F. Ugozzoli, J. Chem. Soc., Chem. Commun., 1989, 500.
20. K. Kobayashi, Y. Asakawa, Y. Kato and Y. Aoyama, J. Am. Chem. Soc., 1992, 114, 10307.
21. K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi and Y. Aoyama, J. Am. Chem. Soc., 1993, 115, 2648.
22. D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Cordova, L. A. Godinez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart and D. J. Williams, J. Am. Chem. Soc., 1995, 117, 127.
23. R. Ballardini, V. Balzani, A. Credi, C. L. Brown, R. E. Gillard, M. Montalti, D. Philp, J. F. Stoddart, M. Venturi, A. J. P. White, B. J. Williams and D. J. Williams, J. Am. Chem. Soc., 1997, 119, 12503.
24. M. Asakawa, P. R. Ashton, W. Hayes, H. M. Janssen, E. W. Meijer, S. Menzer, D. Pasini, J. F. Stoddart, A. J. P. White and D. J. Williams, J. Am. Chem. Soc., 1998, 120, 920.
25. (a) S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami and K. Tanabe, J. Am. Chem. Soc., 2000, 122, 3746;
26. (b) S. Tsuzuki, K. Honda, T. Tadafumi, M. Mikami and K. Tanabe, J. Phys. Chem. A, 2002, 106, 4423.
27. A. Arduini, F. F. Nachtigall, A. Pochini, A. Secchi and F. Ugozzoli, Supramol. Chem., 2000, 12, 273.
28. A. Arduini, G. Giorgi, A. Pochini, A. Secchi and F. Ugozzoli, Tetrahedron, 2001, 57, 2411.
29. Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA, 2001.
30. Numerical polarization basis sets in the SVWN (Slater, Vosko, Wilk, Nusair) model. Review of density functional theory (a) R. O. Jones and O. Gunnarssons, Rev. Mod. Phys., 1989, 61, 689R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford Univ. Press, Oxford, 1989; (b) J. K. Labanowky and J. W. Andzelm, ed. Density Functional Methods in Chemistry, Springer Verlag, New York, 1991.
31. Numerical polarization basis sets in the SVWN (Slater, Vosko, Wilk, Nusair) model. Review of density functional theory (a) R. O. Jones and O. Gunnarssons, Rev. Mod. Phys., 1989, 61, 689R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford Univ. Press, Oxford, 1989; (b) J. K. Labanowky and J. W. Andzelm, ed. Density Functional Methods in Chemistry, Springer Verlag, New York, 1991.
32. Numerical polarization basis sets in the SVWN (Slater, Vosko, Wilk, Nusair) model. Review of density functional theory (a) R. O. Jones and O. Gunnarssons, Rev. Mod. Phys., 1989, 61, 689R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford Univ. Press, Oxford, 1989; (b) J. K. Labanowky and J. W. Andzelm, ed. Density Functional Methods in Chemistry, Springer Verlag, New York, 1991.
33. P. O. Widmark, P. A. Malmqvist and B. O. Roos, Theor. Chim. Acta, 1990, 79, 290.
34. J. A. Platts, Phys. Chem. Chem. Phys., 2000, 2, 973.
35. 2, see I. F. Tupisyn and A. S. Popov, Russ. J. Gen. Chem., 2001, 71, 89 (translated from Zh. Obshch. Khim, 2001, 71, 97) and references therein.
36. S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami and K. Tanabe, J. Phys. Chem. A, 2002, 106, 4423.
37. C. Møller and M. S. Plesset, Phys. Rev., 1934, 46, 618.
38. M. Head-Gordon, J. A. Pople and M. J. Frisch, Chem. Phys. Lett., 1988, 153, 503.
39. J. A. Pople, M. Head-Gordon and K. Raghavachari, J. Chem. Phys., 1987, 87, 5968.
40. G. E. Scuseria and H. F. Schafer, J. Chem. Phys., 1989, 90, 3700.