Counterion effects on the cation-π interaction between alkaline earth cations and benzene

Journal of Physical Chemistry A

Volumn 106, Issue 46, 2002, Pages 11215-11220

  Cheng, Yu Hui ^a   Liu, Lei ^b   Fu, Yao ^a   Chen, Rong ^a   Li, Xiao Song ^c   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Howard Hughes Medical Institute   (United States)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BERYLLIUM; CHARGE TRANSFER; ELECTRONS; MAGNESIUM PRINTING PLATES; NEGATIVE IONS;

COUNTERION EFFECTS;

BENZENE;

EID: 0037153307     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp020121g     Document Type: Article

References (38)

1. (a) Ma, J.C.; Dougherty, D.A. Chem. Rev. 1997, 97, 1303.
2. (b) Gokel, G.W.; De Wall, S.L.; Meadows, E.S. Eur. J. Org. Chem. 2000, 2967.
3. (c) Kim, K.S.; Tarakeshwar, P.; Lee, J.Y. Chem. Rev. 1000, 100, 4145.
4. (a) Duffy, E.M.; Kowalczyk, P.J.; Jorgensen, W.L. J. Am. Chem. Soc. 1993, 115, 9271.
5. (b) Luhmer, M.; Bartik, K.; Dejaegere, A.; Bovy, P.; Reisse, J. Bull. Soc. Chim. Fr. 1994, 131, 603.
6. (c) Lee, J.Y.; Lee, S.J.; Choi, H.S.; Ho, S.J.; Kim, K.S.; Ha, T.-K. Chem. Phys. Lett. 1995, 232, 67.
7. (d) Caldwell, J.W.; Kollman, P.A. J. Am. Chem. Soc. 1995, 117, 4177.
8. (e) Mecozzi, S.; West, P., Jr.; Dougherty, D.A. J. Am. Chem. Soc. 1996, 118, 8, 2307.
9. (f) Mecozzi, S.; West, A.P., Jr.; Dougherty, D.A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10566.
10. (g) Cubero, E.; Luque, F.J.; Orozco, M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5976.
11. (h) Chipot, C.; Maigret, B.; Pearlman, D.A.; Kollman, P.A. J. Am. Chem. Soc. 1996, 118, 2998.
12. (i) Nicholas, J.B.; Hay, B.P. J. Phys. Chem. A 1999, 103, 9815.
13. (j) Minoux, H.; Chipot, C. J. Am. Chem. Soc. 1999, 121, 10366.
14. (k) Dunbar, R.C. J. Phys. Chem. A 1998, 102, 8946.
15. (l) Jiang, H.-L.; Zhu, W.-L.; Tan, X.-J.; Chen, J.-Z.; Zhai, Y.-F.; Liu, D.-X.; Chen, K.-X.; Ji, R.-Y. Acta Chim. Sin. 1999, 57, 860.
16. (m) Amicangelo, J.C.; Armentrout, P.B. Jr. Phys. Chem. A 2000, 104, 11420.
17. (n) Nicholas, J.B.; Hay, B.P.; Dixon, D.A. J. Phys. Chem. A 1999, 103, 1394.
18. (o) Gapeev, A.; Dunbar, R.C. J. Am. Chem. Soc. 2001, 123, 8360.
19. (a) Ryzhov, V.; Dunbar, R.C. J. Am. Chem. Soc. 1999, 121, 2259.
20. (b) Petrie, S.; Dunbar, R.C. J. Phys. Chem. A 2000, 104, 4480.
21. (c) Pandey, R.; Rao, B.K.; Jena, P.; Blanco, M.A. J. Am. Chem. Soc. 2001, 123, 3799.
22. Gapeev, A.; Dunbar, R.C. J. Phys. Chem. A 2000, 104, 4084.
23. Counterion effect was even considered to be important for the prototypical π-alkali cation complexes. For example, see (a) Norrby, P.-O.; Liljefors, T. J. Am. Chem. Soc. 1999, 121, 2303.
24. (b) Bartoli, S.; Roelens, S. J. Am. Chem. Soc. 1999, 121, 11908.
25. (c) Bohmer, V.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 2001, 66, 1900.
26. There are several other recent papers relating to the π-alkaline earth cation interactions. (a) Tan, X.J.; Zhu, W.L.; Cai, M.; Luo, X.M.; Gu, J.D.; Silman, I.; Sussman, J.L.; Jiang, H.L.; Ji, R.Y.; Chen, K.X. Chem. Phys. Lett. 2001, 349, 113.
27. (b) Bonomo, L.; Solari, E.; Scopelliti, R.; Floriani, C. Chem. Eur. J. 2001, 7, 1322.
28. (c) Rodriguez-Cmz, S.E.; Williams, E.R. J. Am. Soc. Mass Spectrom. 2001, 12, 250.
29. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Boys, S.F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
31. Tsuzuki, S.; Yoshida, M.; Uchimaru, T.; Mikami, M. J. Phys. Chem. A 2001, 105, 769.
32. It should be mentioned that recent calculations on alkali cation-benzene complexes showed that the difference between the interaction energy obtained by very large basis set and that obtained with a medium size basis set could be as large as 1-4 kcal/mol. Thus, interaction energies obtained using our finally chosen method, MP2/6-311++g(2d,2p)//MP2/6-31+g*, may also have an error of 1-4 kcal/mol. For more, see Feller, D.; Dixon, D.A.; Nicholas, J.B. J. Phys. Chem. A 2000, 104, 11414.
33. Hobza, P.; Sponer, J.; Reschel, T. J. Comput. Chem. 1995, 11, 1315.
34. 4.
35. 4·dR. Because the M-centroid distance is roughly the same when M is the same, the counterion effects should correlate with R.
36. We thank one of the reviewers for pointing out this important problem.
37. Caldwell, J.W.; Kollman, P.A. J. Am. Chem. Soc. 1995, 117, 4177.
38. Breneman, C.M.; Wiberg, K.B. J. Comput. Chem. 1990, 11, 361.