Geometric effects in olefinic cation-π interactions with alkali metals: A computational study

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 42-49

  Engerer, Laura K ^a   Hanusa, Timothy P ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVE FUNCTION; AROMATIC RINGS; BENZENE MOLECULES; BINDING INTERACTION; COMPUTATIONAL STUDIES; ELECTRON DENSITIES; ENTHALPY OF BINDING; ETHYLENE MOLECULES; FLEXIBLE LIGANDS; GEOMETRIC EFFECTS; GEOMETRIC FACTORS; INTERACTION ENERGIES; NET ENERGY; NONCONJUGATED; POLARIZATION INTERACTIONS;

AROMATIC COMPOUNDS; BENZENE; BINDING ENERGY; DENSITY FUNCTIONAL THEORY; ELECTRONS; ETHYLENE; POSITIVE IONS;

COMPLEXATION;

ALKALI METAL; ALKENE DERIVATIVE; CATION; LITHIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; COMPLEX FORMATION; CONJUGATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; ENERGY TRANSFER; POLARIZATION;

EID: 78650896793     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101307z     Document Type: Article

References (75)

1. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324
2. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250
3. Kim, D.; Hu, S.; Tarakeshwar, P.; Kim, K. S.; Lisy, J. M. J. Phys. Chem. A 2003, 107, 1228-1238
4. Bartoli, S.; Roelens, S. J. Am. Chem. Soc. 2002, 124, 8307-8315
5. Sarri, P.; Venturi, F.; Cuda, F.; Roelens, S. J. Org. Chem. 2004, 69, 3654-3661
6. Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett. 1993, 2, 205-208
7. Arduini, A.; Pochini, A.; Secchi, A. Eur. J. Org. Chem. 2000, 2325-2334
8. Matthews, S. E.; Rees, N. H.; Felix, V.; Drew, M. G. B.; Beer, P. D. Inorg. Chem. 2003, 42, 729-734
9. Ferdani, R.; Barbour, L. J.; Gokel, G. W. J. Supramol. Chem. 2002, 2, 343-348
10. Matthews, S. E.; Schmitt, P.; Felix, V.; Drew, M. G. B.; Beer, P. D. J. Am. Chem. Soc. 2002, 124, 1341-1353
11. Choi, H. S.; Suh, S. B.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12094-12099
12. Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E.; O'Hara, C. T. Angew. Chem., Int. Ed. 2006, 45, 6548-6550
13. Priyakumar, U. D.; Punnagai, M.; Krishna Mohan, G. P.; Sastry, G. N. Tetrahedron 2004, 60, 3037-3043
14. Dinadayalane, T. C.; Hassan, A.; Leszczynski, J. J. Mol. Struct. 2010, 976, 320-323
15. Vijay, D.; Sastry, G. N. Phys. Chem. Chem. Phys. 2008, 10, 582-590
16. Dougherty, D. A. Science 1996, 271, 163-168
17. Nakamura, R. L.; Anderson, J. A.; Gaber, R. F. J. Biol. Chem. 1997, 272, 1011-1018
18. Dougherty, D. A.; Lester, H. A. Angew. Chem., Int. Ed. 1998, 37, 2329-2331
19. De Wall, S. L.; Meadows, E. S.; Barbour, L. J.; Gokel, G. W. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6271-6276
20. Amicangelo, J. C.; Armentrout, P. B. J. Phys. Chem. A 2000, 104, 11420-11432
21. Sunner, J.; Nishizawa, K.; Kebarle, P. J. Phys. Chem. 1981, 85, 1814-1820
22. Macias, A. T.; Norton, J. E.; Evanseck, J. D. J. Am. Chem. Soc. 2003, 125, 2351-2360
23. Feller, D. Chem. Phys. Lett. 2000, 322, 543-548
24. Choi, H. S.; Kim, D.; Tarakeshwar, P.; Suh, S. B.; Kim, K. S. J. Org. Chem. 2002, 67, 1848-1851
25. Gokel, G. W.; De Wall, S. L.; Meadows, E. S. Eur. J. Org. Chem. 2000, 2967-2978
26. Hu, J.; Barbour, L. J.; Gokel, G. W. Chem. Commun. 2001, 1858-1859
27. Hu, J.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2001, 123, 9486-9487
28. Chmely, S. C.; Carlson, C. N.; Hanusa, T. P.; Rheingold, A. L. J. Am. Chem. Soc. 2009, 131, 6344-6345
29. Armentrout, P. B.; Rodgers, M. T. J. Phys. Chem. A 2000, 104, 2238-2247
30. Amicangelo, J. C.; Armentrout, P. B. Int. J. Mass Spectrom. 2001, 212, 301-325
31. Gren, C. K.; Hanusa, T. P.; Rheingold, A. L. Organometallics 2007, 26, 1643-1649
32. Cabarcos, O. M.; Weinheimer, C. J.; Lisy, J. M. J. Chem. Phys. 1999, 110, 8429-8435
33. Te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931-967
34. Guerra, C. F.; Snijders, J. G.; Te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391-403
35. ADF2009.01. SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam.
36. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
38. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206
39. A few examples include: Zheng, X.; Wang, X.; Yi, S.; Wang, N.; Peng, Y. J. Comput. Chem. 2010, 31, 1458-1468
40. Yuan, X.-L.; Zhang, H.; Xie, F.-J. THEOCHEM 2009, 900, 103-109
41. Wang, Y.; Xu, Z.; Gao, Y.; Zhang, L.; Li, H. J. Phys. Chem. A 2009, 113, 7097-7102
42. Zajac, M.; Hrobarik, P.; Magdolen, P.; Foltinova, P.; Zahradnik, P. Tetrahedron 2008, 64, 10605-10618
43. Wu, R.; McMahon, T. B. J. Am. Chem. Soc. 2008, 130, 12554-12555
44. Polfer, N. C.; Oomens, J.; Dunbar, R. C. ChemPhysChem 2008, 9, 579-589
45. Li, Q.; Li, W.; Cheng, J.; Gong, B.; Sun, J. THEOCHEM 2008, 867, 107-110
46. Jover, J.; Bosque, R.; Sales, J. Dalton Trans. 2008, 6441-6453
47. Hallowita, N.; Carl, D. R.; Armentrout, P. B.; Rodgers, M. T. J. Phys. Chem. A 2008, 112, 7996-8008
48. Escudero, D.; Frontera, A.; Quinonero, D.; Deya, P. M. Chem. Phys. Lett. 2008, 455, 325-330
49. Morris, J. J.; Noll, B. C.; Honeyman, G. W.; O'Hara, C. T.; Kennedy, A. R.; Mulvey, R. E.; Henderson, K. W. Chem.-Eur. J. 2007, 13, 4418-4432
50. Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. J. Phys. Chem. A 2007, 111, 10439-10452
51. v symmetry with the TZ2P basis set on an eight-processor 2.8 GHz machine required 38 s with the PBE functional. Starting from the same geometry, we found optimization with the B3LYP functional required 56 min 32 s.
52. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868
53. Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401
54. Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. J. Chem. Phys. 2003, 119, 12129-12137
55. van der Wijst, T.; Guerra, C. F.; Swart, M.; Bickelhaupt, F. M. Chem. Phys. Lett. 2006, 426, 415-421
56. Bickelhaupt, F. M.; Baerends, E. J. In Reviews of Computer Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Wiley-VCH: New York, 2000; Vol. 15, p 1 - 86.
57. Morokuma, K. J. Chem. Phys. 1971, 55, 1236-1244
58. It should be noted that in the energy decomposition sheme used here, interactions are categorized with respect to being within or between fragments. In particular, "polarization" is a phenomenon that refers to the mixing of occupied and virtual orbitals within the same fragment. "Charge transfer" represents the interactions between the occupied molecular orbitals of one fragment and the unoccupied molecular orbitals of the other fragment.
59. Fonseca Guerra, C.; Handgraaf, J. W.; Baerends, E. J.; Bickelhaupt, F. M. J. Comput. Chem. 2004, 25, 189-210
60. Hoyau, S.; Norrman, K.; McMahon, T. B.; Ohanessian, G. J. Am. Chem. Soc. 1999, 121, 8864-8875
61. Curutchet, C.; Bofill, J. M.; Hernández, B.; Orozco, M.; Luque, F. J. J. Comput. Chem. 2003, 24, 1263-1275
62. Krossing, I.; Reisinger, A. Angew. Chem., Int. Ed. 2003, 42, 5725-5728
63. Lau, J. K.-C.; Wong, C. H. S.; Ng, P. S.; Siu, F. M.; Ma, N. L.; Tsang, C. W. Chem.-Eur. J. 2003, 9, 3383-3396
64. Dunbar, R. C.; Petrie, S. Astrophys. J. 2002, 564, 792-802
65. Stanger, A. J. Phys. Chem. A 2008, 112, 12849-12854
66. Soncini, A.; Havenith, R. W. A.; Fowler, P. W.; Jenneskens, L. W.; Steiner, E. J. Org. Chem. 2002, 67, 4753-4758
67. A somewhat more sophisticated model involving the cosine of the θ angle was also explored, but it did not provide appreciably better correlation with the binding energy.
68. Cubero, E.; Luque, F. J.; Orozco, M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5976-5980
69. Tsuzuki, S.; Yoshida, M.; Uchimaru, T.; Mikami, M. J. Phys. Chem. A 2001, 105, 769-773
70. Sauer, J.; Deininger, D. J. Phys. Chem. 1982, 86, 1327-1332
71. Millefiori, S.; Alparone, A. THEOCHEM 1998, 422, 179-190
72. Moszynski, R.; Wormer, P. E. S.; Jeziorski, B.; van der Avoird, A. J. Chem. Phys. 1995, 103, 8058-8074
73. 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
74. Amunugama, R.; Rodgers, M. T. Int. J. Mass Spectrom. 2003, 227, 339-360
75. Suresh, C. H.; Gadre, S. R. J. Phys. Chem. A 2007, 111, 710-714