NMR studies of nonplanar porphyrins. Part 2. Effect of nonplanar conformational distortions on the porphyrin ring current

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1997, Pages 839-844

  Medforth, Craig J ^a   Muzzi, Cinzia M ^a   Shea, Kalyn M ^a   Smith, Kevin M ^a   Abraham, Raymond J ^b   Jia, Songling ^c   Shelnutt, John A ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c SANDIA NATIONAL LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001232306     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a603413f     Document Type: Article

References (48)

1. L. Pauling, J. Phys. Chem., 1946, 4, 673.
2. F. London, J. Phys. Radium, 1937, 8, 397.
3. J. A. Pople, J. Phys. Chem., 1956, 24, 1111.
4. U. Fleischer, W. Kutzelnigg, P. Lazzeretti and V. Muhlenkamp, J. Am. Chem. Soc., 1994, 116, 5298.
5. M. Prato, T. Suzuki, F. Wudl, V. Lucchini and M. Maggini, J. Am. Chem. Soc., 1993, 115, 7876.
6. T. Fukazawa, S. Usui, K. Tanimoto and Y. Hirai, J. Am. Chem. Soc., 1994, 116, 8169.
7. K. J. Cross and M. J. Crossley, Aust. J. Chem., 1992, 45, 991.
8. (a) M. Gosmann and B. Franck, Angew. Chem., Int. Ed. Engl., 1986, 25, 1100;
9. (b) E. LeGoff and O. G. Weaver, J. Org. Chem., 1987, 52, 710.
10. (a) R. J. Abraham and K. M. Smith, J. Am. Chem. Soc., 1983, 105, 5734;
11. (b) R. J. Abraham, K. M. Smith, D. A. Goff and F. W. Bobe, J. Am. Chem. Soc., 1985, 107, 1085;
12. (c) K. M. Smith, F. W. Bobe, D. A. Goff and R. J. Abraham, J. Am. Chem. Soc., 1986, 108, 1111.
13. (a) R. J. Abraham, G. R. Bedford and B. Wright, Org. Magn. Reson., 1982, 18, 45;
14. (b) R. J. Abraham and C. J. Medforth, Magn. Reson. Chem., 1987, 25, 432;
15. (c) R. J. Abraham and C. J. Medforth, Magn. Reson. Chem., 1988, 26, 334;
16. (d) R. J. Abraham and C. J. Medforth, Magn. Reson. Chem., 1988, 26, 803;
17. (e) R. J. Abraham and I. Marsden, Tetrahedron, 1992, 48, 7489.
18. A. Gaudemer, M. Gouedard and C. Riche, J. Chem. Res. (M), (a) 1978, 548; (b) 1978, 560.
19. (a) R. J. Abraham, K. M. Smith, D. A. Goff and J. J. Lai, J. Am. Chem. Soc., 1982, 104, 4332;
20. (b) R. J. Abraham, C. J. Medforth, K. M. Smith, D. A. Goff and D. J. Simpson, J. Am. Chem. Soc., 1987, 109, 4786.
21. (a) H. K. Hombrecher, G. Horter and C. Arp, Tetrahedron, 1992, 48, 9451;
22. (b) J. Takeda and M. Sato, Tetrahedron Lett., 1994, 35, 3565;
23. (c) W. W. Kalisch and M. O. Senge, Tetrahedron Lett., 1996, 37, 1183;
24. (d) M. Miura, S. A. Majumder, J. D. Hobbs, M. W. Renner, L. R. Furenlid and J. A. Shelnutt, Inorg. Chem., 1994, 33, 6078.
25. (a) K. M. Barkigia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner and K. M. Smith, J. Am. Chem. Soc., 1990, 112, 8851;
26. (b) K. M. Barkigia, M. W. Renner, L. R. Furenlid, C. J. Medforth, K. M. Smith and J. Fajer, J. Am. Chem. Soc., 1993, 115, 3627;
27. (c) M. W. Renner, K. M. Barkigia, Y. Zhang, C. J. Medforth, K. M. Smith and J. Fajer, J. Am. Chem. Soc., 1994, 116, 8582.
28. (a) J. A. Shelnutt, C. J. Medforth, M. D. Berber, K. M. Barkigia and K. M. Smith, J. Am. Chem. Soc., 1991, 113, 4077;
29. (b) L. D. Sparks, C. J. Medforth, M.-S. Park, J. R. Chamberlain, M. R. Ondarias, M. O. Senge, K. M. Smith and J. A. Shelnutt, J. Am. Chem. Soc., 1993, 115, 581;
30. (c) C. J. Medforth, J. D. Hobbs, M. R. Rodriguez, R. J. Abraham, K. M. Smith and J. A. Shelnutt, Inorg. Chem., 1995, 34, 1333.
31. (a) T. Ema, M. O. Senge, N. Y. Nelson and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1994, 33, 1879;
32. (b) M. O. Senge, T. Ema and K. M. Smith, J. Chem. Soc., Chem. Commun., 1995, 733;
33. (c) W. Jentzen, J. D. Hobbs, M. C. Simpson, K. K. Taylor, T. Ema, N. Y. Nelson, C. J. Medforth, K. M. Smith, M. Veyrat, M. Mazzanti, R. Ramasseul, J.-C. Marchon, T. Takeuchi, W. A. Goddard III and J. A. Shelnutt, J. Am. Chem. Soc., 1995, 117, 11 085.
34. C. J. Medforth, C. M. Muzzi, K. M. Shea, K. M. Smith, R. J. Abraham, S. Jia and J. A. Shelnutt, preceding paper.
35. W. R. Scheidt and Y. J. Lee, Struct. Bonding (Berlin), 1987, 6, 1.
36. (a) E. Pretsch, T. Clerc, J. Seibl and W. Simon, Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, Berlin, 1989;
37. (b) J. Emsley, J. Feeney and L. H. Sutcliffe, High Resolution NMR Spectroscopy, Pergamon Press, Oxford, 1966, vol. 2, Appendix B;
38. (c) R. K. Harris and B. P. Howes, J. Mol. Spectrosc., 1968, 28, 191.
39. A. Streitwieser Jr., Molecular Orbital Theory for Organic Chemists, Wiley, London, 1961, p. 489.
40. Landolt-Bornstein, Structure Data of Polyatomic Molecules, Springer-Verlag, New York, 1976, vol. 7.
41. (a) X.-Z. Song, W. Jentzen, S. Jia, L. Jaquinod, D. J. Nurco, C. J. Medforth, K. M. Smith and J. A. Shelnutt, J. Am. Chem. Soc., 1996, 118, 12975;
42. (b) L. Jaquinod, C. J. Medforth and K. M. Smith, unpublished results.
43. T. R. Janson and J. J. Katz, in The Porphyrins, ed. D. Dolphin, Academic Press, New York, 1979, vol. 4, p. 13.
44. G. A. Jeffrey and W. Saenger, in Hydrogen Bonding in Biological Structures, Springer-Verlag, New York, 1991, p. 30.
45. H. F. Friedrich, Z. Naturforsch., Teil B, 1965, 20, 1021.
46. J. W. Lauher and J. A. Ibers, J. Am. Chem. Soc., 1974, 96, 4447.
47. W. R. Scheidt, J. A. Cunningham and J. L. Hoard, J. Am. Chem. Soc., 1973, 95, 8289.
48. A. L. van Geet, Anal. Chem., 1970, 42, 679.