9-substituted triptycene as a probe for the study of internal rotation around a C-PH bond in the solid state: A single crystal EPR study at variable temperature

Journal of Physical Chemistry

Volumn 100, Issue 26, 1996, Pages 10861-10868

  Ramakrishnan, Geetha ^a   Jouaiti, Abdelaziz ^a   Geoffroy, Michel ^a   Bernardinelli, Gérald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013414494     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp960836h     Document Type: Article

References (56)

1. Internal Rotation in Molecules; Orville-Thomas, W. J., Ed.; John Wiley: London, 1974.
2. Durig, J. R.; Gounev, T. K.; Lee, M. S.; Little, T. S. J. Mol. Struct. 1994, 327, 23-53.
3. Janzen, E. G. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Eds.; Intersciences Publisher: New York, 1971; Vol. 6, pp 177-217.
4. Hudson, A.; Luckhurst, G. R. Chem. Rev. 1969, 69, 191-225.
5. Freed, J. H.; Fraenkel, G. K. J. Chem. Phys. 1963, 39, 326-348.
6. McCalley, R. C.; Shimschick, E. J.; McConnell, H. M. Chem. Phys. Lett. 1972, 13, 115-119.
7. Barzaghi, M.; Gamba, A; Oliva, Cesare; Branca, Mario. Int. Rev. Phys. Chem. 1987, 6, 315-336.
8. Huang, R. H.-H.; Kivelson, D. J. Magn. Reson. 1974, 14, 202-222.
9. Heinzer, J. Mol. Phys. 1971, 22, 167-177.
10. Brustolon, M.; Segre, U. J. Chim. Phys. Phys.-Chim. Biol. 1994, 91, 1820-1829.
11. Ohigashi, H.; Kurita, Y. Bull. Chem. Soc. Jpn. 1968, 41, 275-284.
12. Sjöqvist, L.; Benetis, N. P.; Lund, A.; Maruani. J. Chem. Phys. 1991, 156, 457-464.
13. Benetis, N. P.; Lindgren, M.; Lee, H.-S.; Lund, A. Appl. Magn. Reson. 1990, 1, 267-281.
14. Benetis, N. P.; Mahgoub, A.; Lund, A.; Nordh, U. Chem. Phys. Lett. 1994, 218, 551-556.
15. Peric, M.; Ravkin, B.; Dulcic, A. Chem. Phys. Lett. 1986, 126, 574-578.
16. Benetis, N. P.; Sjöqvist, L.; Lund, A.; Maruani, J. J. Magn. Reson. 1991, 95, 523-535.
17. Hayes, R. G.; Steible, D. J., Jr.; Tolles, W. M.; Hunt, J. W. J. Chem. Phys. 1970, 53, 4466-4469.
18. Bogan, C. Ph.D. Thesis, The University of Alabama, 1972.
19. Kispert, L. D.; Chang, K.; Bogan, C. M. J. Chem. Phys. 1973, 77, 629-633.
20. Bogan, C. M.; Kispert, L. D. J. Chem. Phys. 1972, 57, 3109-3120.
21. Kispert, L. D.; Bowman, M. K.; Norris, J. R.; Brown, M. S. J. Chem. Phys. 1982, 76, 26-30.
22. Oki, M. Acc. Chem. Res. 1990, 23, 351-356.
23. (a) Oki, M.; Matsusue, M.; Akinaga, T.; Matsumoto, Y.; Toyota, S. Bull. Chem. Soc. Jpn. 1994, 67, 2381-2387.
24. (b) Nakamura, M.; Oki, M. Bull. Chem. Chem. Soc. Jpn. 1975, 48, 2106-2111.
25. Oki, M. Angew. Chem., Int. Ed. Engl. 1976, 15, 87-93.
26. Imashiro, F.; Hirayama, K.; Terao, T.; Saika, A. J. Am. Chem. Soc. 1987, 109, 729-733.
27. Yamamoto, G.; Kuwahara, K.; Inoue, K. Chem. Lett. 1995, 351-352.
28. Sakakibara, K.; Allinger, N. L. J. Org. Chem. 1995, 60, 4044-4050.
29. James, F.; Roos, M. CERN Program Library; CERN: Geneva, Switzerland, 1976.
30. Iwasaki, M. J. Magn. Reson. 1974, 16, 417-423.
31. Frisch, F. M.; Head-Gordon, M.; Trucks, G. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M.; Binkley, J. S.; Gonzalez, C.; Defrees, D. J.; Fox, D. J.; Whiteside, R. A.; Seeger, R.; Melius, C. F.; Baker, J.; Martin, R. L.; Kahn, L. R.; Stewart, J. J. P.; Topiol, S.; Pople, J. Gaussian 90; Gaussian, Inc.: Pittsburgh, PA, 1990.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. V.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. Gaussian 92/DFT, Revision G.2; Gaussian Inc.: Pittsburgh, PA, 1992.
33. Blanc, E.; Schwarzenbach, D.; Flack, H. D. J. Appl. Crystallogr. 1991, 24, 1035-1041.
34. Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; Declercq, J.-P.; Woolfson, M. M. A System of Computer Programs for the Automatic Solution of Crystal structures from X-Ray Diffraction Data; University of York and Louvain-la-Neuve: England and Belgium, 1987.
35. Hall, S. R., Flack, H. D., Stewart, J. M., Eds. XTAL3.2 User's Manual; Universities of Western Australia and Maryland: Nedlands, Australia and College Park, MD, 1992.
36. Johnson, C. K. ORTEP II. Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
37. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974.
38. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881.
39. Bernardinelli, G.; Flack, H. D. Acta Crystallogr. 1985, A41, 500-511.
40. Le Page, Y. J. Appl. Crystallogr. 1987, 20, 264-269.
41. Tabushi, I.; Yoshida, Z.; Aoyama, Y. Bull. Chem. Soc. Jpn. 1974, 47, 3079-3083.
42. Freijee, F. J. M.; Stam, C. H. Acta Crystallogr. 1980, B36, 1247-1249.
43. Van der Putten, N.; Stam, C. H. Acta Crystallogr. 1980, B36, 1250-1252.
44. Smit, F.; Stam, C. H. Acta Crystallogr. 1980, B36, 1254-1256.
45. Schomburg, D.; Sheldrick, W. S. Acta Crystallogr. 1975, B31, 2427-2431.
46. Reichel, C. L.; McBride, J. M. J. Am. Chem. Soc. 1977, 99, 6758-6760.
47. Geoffroy, M.; Ginet, L.; Lucken, E. A. Mol. Phys. 1976, 31, 745-754.
48. Geoffroy, M.; Lucken, E. A. C.; Mazeline, C. Mol. Phys. 1974, 28, 839-845.
49. Tordo, P. In The Chemistry of Organophosphorus Compounds; Patai, P., Hartley, F., Eds.; J. Wiley: New York, 1990; Vol. 1, p 437.
50. Morton, J. R.; Preston, K. F. J. Magn. Reson. 1978, 30, 577-582.
51. (a) Bowman, M.; Kevan, L.; Schwartz, R. N. Chem. Phys. Lett. 1975, 30, 208-211.
52. (b) Schlick, S; Kevan, L. J. Magn. Reson. 1976, 22, 171-181.
53. (c) Schlick, S.; Kevan, L. J. Magn. Reson. 1976, 21, 129-133.
54. 3), it was judicious to renumber the atoms taking into account the asymmetric unit. This numbering is shown in Figure 1.
55. In this calculation the three tensors expressed in the experimental reference frame are added, and the resulting tensor is divided by three and diagonalized.
56. The experimental proton dipolar tensor exhibits an axial symmetry that is more pronounced than for the calculated tensor. This probably reflects a modest precision on the measurement of the proton splittings, at 77K, due to an overlap of two sites in the planes a*c and bc.