Creating Three Pentacoordinated Carbons in a Six-Membered Ring. An Atoms-in-Molecules and Electron-Localization Function Study on the Trishomocyclopropenyl Cation and Phosphorus, Sulfur, Arsenic, and Selenium Analogues

Journal of Physical Chemistry A

Volumn 107, Issue 44, 2003, Pages 9434-9446

  Werstiuk, Nick Henry ^a   Wang, Yi Gui ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DELOCALIZATION; HOMOCONJUGATED SPECIES; VALENCE BASINS;

ARSENIC COMPOUNDS; BONDING; CARBON; CHEMICAL BONDS; ELECTRONS; MOLECULAR STRUCTURE; POSITIVE IONS; SELENIUM; TOPOLOGY;

AROMATIC COMPOUNDS;

EID: 0242708937     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp030741x     Document Type: Article

References (51)

1. Winstein, S. J. Am. Chem. Soc. 1959, 81, 6524.
2. Winstein, S.; Sonnenberg, J. J. Am. Chem. Soc. 1961, 83, 3235, 3244.
3. Masamune, S.; Sakai, M.; Jones, A. V. K.; Nakashima, T. Can. J. Chem. 1974, 52, 855.
4. Olah, G. A.; Prakash, G. K. S.; Rawdah, T. N.; Whittaker, D.; Rees, J. C. J. Am. Chem. Soc. 1979, 101, 3935.
5. Haywood-Farmer, J. Chem. Rev. 1974, 74, 315.
6. Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1978, 17, 106.
7. Childs, R. F. Acc. Chem. Res. 1984, 17, 347.
8. Williams, R. F. Chem. Rev. 2001, 101, 1185.
9. Olah, G. A.; Prakash, G. K. S.; Williams, R. E.; Field, L. D.; Wade, K. Hypercarbon Chemistry; John Wiley & Sons: New York, 1987.
10. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
11. Popelier, P. L. A. Atoms in Molecule. An Introduction; Pearson Education; Harlow, U.K., 1999.
12. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397.
13. Bader, R. F. W.; Stephens, M. E. J. Am. Chem. Soc. 1975, 97, 7391.
14. Fradera, X.; Austen, M. A.; Bader, R. F. W. J. Phys. Chem. A 1999, 103, 304.
15. Silvi, B.; Savin, A. Nature 1994, 371, 683.
16. Noury, S.; Colonna, A.; Savin, A.; Silvi, B. J. Mol. Struct. (THEOCHEM) 1998, 450, 59.
17. Savin, A.; Silvi, B.; Colonna, F. Can. J. Chem. 1996, 74, 1088.
18. Cremer, D.; Kraka, E.; Slee, T. S.; Bader, R. F. W.; Lau, C. D. H.; Nguyen-Dang, T. T.; MacDougall, P. J. J. Am. Chem. Soc. 1983, 105, 5069.
19. Szabo, K. J.; Kraka, E.; Cremer, D. J. Org. Chem. 1996, 61, 2783.
20. Cremer, D.; Childs, R. L.; Kraka, E. In The Chemistry of the cyclopropyl group; Rappotpart, Z., Ed.: John Wiley & Sons Ltd: New York, 1995; Vol. 2, pp 339-410.
21. Werstiuk, N. H.; Muchall, H. M. J. Mol. Struct. (THEOCHEM) 1999, 463, 225.
22. Werstiuk, N. H.; Muchall, H. M. J. Phys. Chem. A 2000, 104, 2054.
23. Werstiuk, N. H.; Muchall, H. M.; Noury, S. J. Phys. Chem. A 2000, 104, 11601.
24. Werstiuk, N. H.; Wang, Y. G. J. Phys. Chem. A 2001, 105, 11515.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
26. 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.; Carami, 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.1; Gaussian, Inc.: Pittsburgh, PA, 1998.
27. Biegler-König, F. W.; Bader, R. F. W.; Tang, T.-H. J. Comput. Chem. 1982, 3, 317.
28. Biegler-König, F.; Schönbohm, J. AIM2000, version 2.0; Innovation Software: Bielefeld, Germany, 2002.
29. Cremer, D.; Kraka, E. Angew. Chem., Int. Ed. Engl. 1984, 23 (8), 627.
30. Chan, W.-T.; Hamilton, I. P. J. Chem. Phys. 1998, 108 (6), 2473.
31. Malta, C. F. AIMDELOC; QCPE0802; Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University: Bloomington, IN.
32. Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. TopMod; Université Pierre et Marie Curie: Paris, 1997.
33. Noury, S.; Krokidis, X.; Fuster, F.; Silvi, B. Comput. Chem. 1999, 23, 597.
34. Pepke, E.; Murray, J.; Lyons, J.; Hwu, T.-Y. SciAn, version 1.21; Alpha: Supercomputer Computations Research Institute: Florida State University, Tallahassee, EL, 1991.
35. Wang, Y.-G.; Werstiuk, N. H. J. Comput. Chem. 2003, 24 (3), 379.
36. Sieber, S.; Schleyer, P. V. R.; Otto, A. H.; Gauss, J.; Reichel, F.; Cremer, D. J. Phys. Org. Chem. 1993, 6, 445.
37. Honegger, E.; Heilbronner, E.; Schmelzer, A. Nouv. J. Chim. 1982, 6 (11), 519.
38. Honegger, E.; Heilbronner, E.; Schmelzer, A.; Wang, J.-Q. Isr. J. Chem. 1982, 22 (1), 3.
39. Calatayud, M.; Andres, J.; Beltran, A.; Silvi, B. Theor. Chem. Acc. 2001, 105 (4-5), 299-308.
40. Noury, S.; Silvi, B.; Gillespie, R. J. Inorg. Chem. 2002, 41 (8), 2164.
41. Cioslowski, J.; Mixon, T. Inorg. Chem. 1993, 32, 3209.
42. Rauk, A.; Sorensen, T. S.; Maerker, C.; Carneiro, M.; Sieber, S.; Schleyer, P. V. R. J. Am. Chem. Soc. 1996, 118, 3761.
43. Rauk, A.; Sorensen, T. S.; Schleyer, P. V. R. J. Chem. Soc., Perkin Trans. 2 2001, 867.
44. Bader, R. F. W.; Johnson, S.; Tang, T.-H.; Popelier, P. L. A. J. Phys. Chem. 1996, 100, 15398.
45. Kohout, M. Int. J. Quantum Chem. 2001, 83, 324.
46. Sagar, R. P.; Ku, A. C.; Simith, V. H., Jr. Can. J. Chem. 1988, 66, 1005.
47. Levit, C.; Sarfatti, J. Chem. Phys. Lett. 1997, 281, 157
48. Hamilton, I. P. Chem. Phys. Lett. 1998, 297, 261
49. Levit, C.; Sarfatti, J. Chem. Phys. Lett. 1998, 297, 263
50. Kohout, M. Int. J. Quantum Chem. 2002, 81, 12.
51. Burckhardt, A.; Wedig, U.; von Schnering, H. G.; Savin, A. Z. Anorg. Aug. Chem. 1993, 619, 437.