Assessment of σ-diatropicity of the cyclopropane molecule

Journal of Physical Chemistry A

Volumn 111, Issue 33, 2007, Pages 8163-8169

  Pelloni, Stefano ^a   Lazzeretti, Paolo ^a   Zanasi, Riccardo ^b  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CURRENT DENSITY; MAGNETIC FIELDS; MAGNETIC PROPERTIES; MAGNETIC SHIELDING; MATHEMATICAL MODELS;

CURRENT DENSITY FIELDS; DIATROPICITY; MAGNETIC TENSORS; MAGNETROPICITY;

PROPANE;

EID: 34548544953     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0710638     Document Type: Article

References (59)

1. Walsh, A. D. Nature 1947, 159, 712.
2. Walsh, A. D. Trans. Faraday Soc. 1948, 45, 179.
3. Walsh, A. D. J. Chem. Soc. 1953, 2260. Consider also the series of nine following papers, pp 2266-2331 of the same issue.
4. Coulson, C. A.; Moffitt, W. E. J. Chem. Phys. 1947, 15, 151.
5. Coulson, C. A.; Moffitt, W. E. Philos. Mag. 1948, 40, 1.
6. Dewar, M. J. S. J. Am. Chem. Soc. 1984, 106, 669.
7. Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1985, 107, 3800.
8. Cremer, D.; Gauss, J. J. Am. Chem. Soc. 1986, 108, 7467.
9. Exner, K.; von Ragué Schleyer, P. J. Phys. Chem. A 2001, 105, 3407.
10. Wiberg, K.; Nist, B. J. J. Am. Chem. Soc. 1961, 83, 1226.
11. Burke J. J.; Lauterbur, P. C. J. Am. Chem. Soc. 1964, 86, 1870.
12. Zilm, K.; Beeler, A. J.; Grant, D. M.; Michl, J.; Chou, T.; Allred, E. L. J. Am. Chem. Soc. 1981, 103, 2119.
13. Aldrich, P. D.; Kukolich, S. G.; Campbell, E. J.; Read, W. G. J. Am. Chem. Soc. 1983, 105, 5569.
14. Lukins, P. B.; Laver, D. R.; Buckingham, A. D.; Ritchie, G. L. D. J. Phys. Chem. 1985, 89, 1309.
15. Jackman, L. M.; Sternhell, S. Application of Nuclear Magnetic Resonance in Organic Chemistry, 2nd Ed; Pergamon Press: Braunschweig, 1969.
16. Dauben, H. J.; Wilson, J. D.; Laity, J. L. In Non-Benzenoid Aromatics; Snyder, J. P. Ed; Academic Press: New York, 1971; Vol. 2, and references therein.
17. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. J. Mol. Struct. 1988, 181, 93.
18. Moran, D.; Manoharan, M.; Heine, T.; von Ragué Schleyer, P. Org. Lett. 2003, 5, 23.
19. Pascal, P. Compt. Rend. 1925, 181, 656.
20. Pascal, P. Chimie Général; Masson: Paris, 1959.
21. Barter, C.; Meisenheimer, R. G.; Stevenson, D. P. J. Phys. Chem. 1960, 64, 1312.
22. Flygare, W. H. Chem. Rev. 1974, 74, 653.
23. Lacher, J. R.; Pollock, J. W.; Park, J. D. J. Chem. Phys. 1952, 20, 1047.
24. Poulter, C. D.; Boikess, R. S.; Brauman, J. I.; Winstein, S. J. Am. Chem. Soc. 1972, 94, 2291.
25. Hahn, R. C.; Howard, P. C. J. Am. Chem. Soc. 1972, 94, 3143.
26. Patel, D. J.; Howden, M. H.; Roberts, J. D. J. Am. Chem. Soc. 1963, 85, 3218.
27. Bettinger, H. F.; Pak, C. H.; Xie, Y. M.; von Ragué Schleyer, P.; Schaefer, H. F. J. Chem. Soc. Perkin Trans. 1999, 2, 2377.
28. Jiao, H.; Nagelkerke, R.; Kurtz, H. A.; Williams, R. V.; Borden, W. T.; von Ragué Schleyer, P. J. Am. Chem. Soc. 1997, 119, 5921.
29. Sauers, R. R.; Sonnet, P. E. Tetrahedron 1964, 20, 1029.
30. Sauers, R. R. Tetrahedron 1998, 54, 337.
31. von Ragué Schleyer, P.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317.
32. Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Mühlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298.
33. Ferraro, M. B.; Faglioni, F.; Ligabue, A.; Pelloni, S.; Lazzeretti, P. Magn. Reson. Chem. 2005, 43, 316.
34. Pelloni, S.; Ligabue, A.; Lazzeretti, P. Org. Lett. 2004, 6, 4451.
35. Soncini, A. P.; Fowler, W.; Lazzeretti, P.; Zanasi, R. Chem. Phys. Lett. 2005, 401, 164.
36. Lazzeretti, P.; Zanasi. R. J. Am. Chem. Soc. 1983, 105, 12.
37. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223.
38. Lazzeretti, P.; Malagoli, M.; Zanasi, R. Chem. Phys. Lett. 1994, 220, 299.
39. Lazzeretti, P. Ring Currents, In Progress in Nuclear Magnetic Resonance Spectroscopy; Emsley, J. W., Feeney, J., Sutcliffe, L. H. Eds; Elsevier: The Netherlands, 2000; Vol. 36, pp 1-88,
40. Steiner, E.; Fowler, P. W. J. Phys. Chem. A 2001, 105, 9553.
41. Soncini, A.; Fowler, P. Chem. Phys. Lett. 2004, 396, 174.
42. Soncini, A.; Lazzeretti, P.; Zanasi, R. Chem. Phys. Lett. 2006, 421, 21.
43. Jusélius, J. Theoretical investigation of magnetically induced currents in closed-shell molecules, Dissertation for the degree of Doctor Philosophiae. Department of Chemistry, University of Helsinki, 2004.
44. Jusélius, J.; Sundholm, D.; Gauss, J. J. Chem. Phys. 2004, 121, 3952.
45. Zanasi, R.; Lazzeretti, P.; Malagoli, M.; Piccinini, F. J. Chem. Phys. 1995, 102, 7150.
46. Lazzeretti, P. Electric and magnetic properties of molecules, In Handbook of Molecular Physics and Quantum Chemistry, John Wiley & Sons, Ltd., Chichester, 2003, Vol. 3, Part 1, Chapter 3, pp 53-145.
47. Zanasi, R. J. Chem. Phys. 1996, 105, 1460.
48. Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; von Ragué Schleyer, P. Org. Lett. 2006, 8, 863.
49. Jameson, C. J.; Buckingham, A. D. J. Phys. Chem. 1979, 83, 3366.
50. Jameson, C. J.; Buckingham, A. D. J. Chem. Phys. 1980, 73, 5684.
51. The average Madelung-London-Landau local velocity vanishes at stagnation points so that there is no violation of the uncertainty principle, see the discussion on p 38 of ref 39.
52. Gomes, J. A. N. F. Phys. Rev. A 1983, 28, 559.
53. Pelloni, S.; Faglioni, F.; Zanasi, R.; Lazzeretti, P. Phys. Rev. A 2006, 74, 012506.
54. Pelloni, S.; Lazzeretti, P. Theor. Chem. Ace 2007, 117, 903.
55. Pelloni, S.; Lazzeretti, P. Theor. Chem. Ace 2007, 118, 89.
56. The LINUX and WINDOWS versions of the graphic code used to obtain 3D representations of the stagnation graph and current density vector field of a series of molecules can be downloaded at https://theochem.chimfar.unimo.it/ VED03/cyclopropane.
57. Ligabue, A.; Soncini, A.; Lazzeretti, P. J. Am. Chem. Soc. 2002, 124, 2008.
58. Keith, T. A.; Bader, R. F. W. Can. J. Chem. 1996, 74, 185.
59. -1) for a diamagnetic (paramagnetic) vortex.