Ring currents in tangentially p-p bonded σ-aromatic systems

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6459-6467

  Fowler, Patrick W ^a   Rogowska, Agnieszka ^b   Soncini, Alessandro ^c   Lillington, Mark ^a   Olson, Leif P ^d  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b UNIVERSITY OF WARSAW   (Poland)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MAGNETIC PROPERTIES; MOLECULAR STRUCTURE; NUMERICAL METHODS; PHASE TRANSITIONS;

IPSOCENTRIC RING; MOLECULAR ORBITALS; RING CURRENT; TANGENTIAL BASIS FUNCTION;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; CARBON; HYDROGEN; SILICON;

ARTICLE; CRYSTAL STRUCTURE; ELECTRON; ENERGY; GEOMETRY; MOLECULAR INTERACTION; MOLECULAR MODEL; VIBRATION;

EID: 33747426242     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060788p     Document Type: Article

References (46)

1. (a) Alexandrova, A. N.; Boldyrev, A. I. J. Phys. Chem. A 2003, 107, 554.
2. (b) Havenith, R. W. A.; De Proft, F.; Fowler, P. W.; Geerlings, P. Chem. Phys. Lett. 2005, 407, 391.
3. (c) Li, X.; Kuznetsov, A. E.; Zhang, H.-F.; Boldyrev, A. I.; Wang, L.-S. Science 2001, 291, 859.
4. (d) Kuznetsov, A. E.; Boldyrev, A. I.; Li, X.; Wang, L.-S. J. Am. Chem. Soc. 2001, 123, 8825.
5. (e) Kuznetsov, A. E.; Corbett, J. D.; Wang, L.-S.; Boldyrev, A. I. Angew. Chem., Intl. Ed. 2001, 40, 3369.
6. (f) Fowler, P. W.; Steiner, E.; Havenith, R. W. A. Chem. Phys. Lett. 2001, 342, 85.
7. (g) Fowler, P. W.; Havenith, R. W. A.; Steiner, E. Chem. Phys. Lett. 2002, 359, 530.
8. (h) Zhan, C.-G.; Zheng, F.; Dixon, D. A. J. Am. Chem. Soc. 2002, 124, 14795.
9. (a) Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223.
10. (b) Keith, T. A.; Bader, R. F. W. J. Phys. Chem. A 1993, 99, 3669.
11. (c) Coriani, S.; Lazzeretti, P.; Malagoli, M.; Zanasi, R. Theor. Chim. Acta 1994, 89, 181.
12. (d) Zanasi, R. J. Chem. Phys. 1996, 105, 1460.
13. (e) Steiner, E.; Fowler, P. W. J. Phys. Chem. A 2001, 105, 9553.
14. (f) Steiner, E.; Fowler, P. W. Chem. Commun., 2220.
15. (g) Fowler, P. W.; Steiner, E. Chem. Phys. Lett. 2002, 364, 259.
16. (a) Dewar, M. J. S. Bull. Soc. Chim. Belg. 1979, 88, 957.
17. (b) Cremer, D. Tetrahedron 1988, 44, 7427.
18. (c) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. J. Mol. Struct. 1988, 50, 93.
19. (d) Cremer, D.; Gauss, J. J. Am. Chem. Soc. 1986, 108, 7467.
20. (a) Paquette, L. A. Angew. Chem., Int. Ed. 1978, 17, 106.
21. (b) Stahl, F.; Schleyer, P. v. R.; Jiao, H.; Schaefer, H. F., III; Chen, K.-S.; Allinger, N. L. J. Org. Chem. 2002, 67, 6599.
22. (c) Williams, R. V. Chem. Rev. 2001, 101, 1185.
23. (a) Houk, K. N.; Gandour, R. W. Strozier, R. W.; Rondan, N. G.; Paquette, L. A. J. Am. Chem. Soc. 1979, 101, 6797.
24. (b) Havenith, R. W. A.; Fowler, P. W.; Jenneskens, L. W.; Steiner, E. J. Phys. Chem. A 2003, 107, 1867.
25. (c) Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.
26. (a) Hoffmann, R. Solids and Surfaces: A Chemist's View on Bonding in Extended Structures; VCH Publishers: New York, 1988; pp 3-14.
27. (b) Atkins, P. W. Quanta: A Handbook of Concepts; Oxford University Press: Oxford, UK, 1991; pp 359-357.
28. (c) Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements, 2nd ed.; Butterworth Heinemann: Oxford, UK, 1991; p 1155.
29. (a) Lipkowitz, K. B.; Latter, R. M.; Boyd, D. B. J. Am. Chem. Soc. 1980, 102, 85.
30. (b) Paquette, L. A.; Usui, S. Tetrahedron Lett. 1999, 40, 3499.
31. (c) Baldridge, K. K.; Leahy, J.; Siegel, J. S. Tetrahedron Lett. 1999, 40, 3503.
32. (d) Livant, P. D.; Northcott, J.; Webb, T. R. Book of Abstracts; 219th ACS National Meeting: San Fransisco, CA, 2000.
33. (e) Olson, L. P. Org. Lett. 2000, 2, 3059.
34. Tantillo, D. J.; Hoffmann, R. J. Am. Chem. Soc. 2003, 125, 4042.
35. (a) Becke, A. D. J. Chem. Phys. 2003, 98, 5648.
36. (b) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
37. (c) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
38. (d) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 167.
39. Jaguar 5.0; Schrödinger, LLC: Portland, OR, 2002.
40. 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.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
41. Lazzeretti, P.; Zanasi, R. SYSMO package; University of Modena, 1980; with additional routines for evaluation and plotting of current density by E. Steiner, P. W. Fowler, R. W. A. Havenith, and A. Soncini.
42. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
43. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
44. (c) Wadt, W. R.; Hay, P. J. J. Chem, Phys. 1985, 82, 284.
45. (d) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
46. (e) Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.