Substituent effects in cation-π interactions: A unified view from inductive, resonance, and through-space effects

Journal of Physical Chemistry A

Volumn 115, Issue 22, 2011, Pages 5660-5664

  Sayyed, Fareed Bhasha ^a   Suresh, Cherumuttathu H ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-DONATING SUBSTITUENTS; ELECTRON-WITHDRAWING SUBSTITUENTS; INTERACTION ENERGIES; POLYNOMIAL EQUATION; RESONANCE EFFECT; SUBSTITUENT EFFECT; THROUGH-SPACE EFFECTS; TOTAL INTERACTION ENERGY;

POLYNOMIALS; RESONANCE;

POSITIVE IONS;

CATION; HALOGENATED HYDROCARBON; SODIUM;

ARTICLE; CHEMISTRY; QUANTUM THEORY;

CATIONS; HYDROCARBONS, HALOGENATED; QUANTUM THEORY; SODIUM;

EID: 79958142882     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp202441x     Document Type: Article

References (25)

1. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
2. Mo, G. C. H.; Yip, C. M. Langmuir 2009, 25, 10719-10729.
3. Hamada, F.; Higuchi, Y.;Kondo,Y.; Kabuto,C.; Iki,N. Tetrahedron Lett. 2006, 47, 5591-5593.
4. Yamada, S. Org. Biomol. Chem. 2007, 5, 2903-2912.
5. Meadows, E. S.; De Wall, S. L.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2001, 123, 3092-3107.
6. Hunter, C. A.; Low, C. M. R.; Rotger, C.; Vinter, J. G.; Zonta, C. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 4873-4876.
7. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
8. Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308.
9. Wheeler, S. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 3126-3127.
10. Soteras, L.; Orozco, M.; Luque, F. J. Phys. Chem. Chem. Phys. 2008, 10, 2616-2624.
11. Frenking, G.; Frohlich, N. Chem. Rev. 2000, 100, 717-774.
12. Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51-57.
13. Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96-103.
14. Sayyed, F. B.; Suresh, C. H. Tetrahedron Lett. 2009, 50, 7351-7354.
15. Suresh, C. H.; Alexander, P.; Vijayalakshmi, K. P.; Sajith, P. K.; Gadre, S. R. Phys. Chem. Chem. Phys. 2008, 10, 6492-6499.
16. Exner, O.; Böhm, S. J. Phys. Org. Chem. 2007, 20, 454-462.
17. Suresh, C. H.; Gadre, S. R. J. Am. Chem. Soc. 1998, 120, 7049-7055.
18. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
19. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799.
20. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, J., 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.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian Inc.: Wallingford CT, 2004.
22. Reddy, S. A.; Sastry, G. N. J. Phys. Chem. A 2005, 109, 8893-8903.
23. Nolan, E. M; Linck, R. G. J. Am. Chem. Soc. 2000, 122, 11497-11506.
24. Silva, P. J. J. Org. Chem. 2009, 74, 914-916.
25. Sayyed, F. B.; Suresh, C. H.; Gadre, S. R. J. Phys. Chem. A 2010, 114, 12330-12333.