Structural studies of peri-interactions and bond formation between electron-rich atomic centres and N-phenylcarboxamides or nitroalkenyl groups

Organic and Biomolecular Chemistry

Volumn 3, Issue 18, 2005, Pages 3273-3283

  O'Leary, Jane ^a   Formosa, Xavier ^a   Skranc, Wolfgang ^a   Wallis, John D ^a  

^a NOTTINGHAM TRENT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; CRYSTALLOGRAPHY; NAPHTHALENE; NEGATIVE IONS;

BOND FORMATIONS; NAPHTHALENE SYSTEMS; PARTIAL CONJUGATION;

BIOCHEMISTRY;

EID: 26444455623     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506045a     Document Type: Article

References (68)

1. H. B. Bürgi, J. D. Dunitz and E. Schefter, J. Am. Chem. Soc., 1973, 95, 5065.
2. H. B. Bürgi and J. D. Dunitz, in Structure Correlation, ed. H. B. Bürgi and J. D. Dunitz, VCH, Weinheim, 1994, p. 205.
3. A. S. Cieplak, in Structure Correlation, ed. B. H. Bürgi and J. D. Dunitz, VCH, Weinheim, 1994, p. 205.
4. W. B. Schweizer, G. Procter, M. Kaftory, M. and J. D. Dunitz, Helv. Chim. Acta, 1978, 61, 2783.
5. P. C. Bell and J. D. Wallis, Chem. Commun., 1999, 257.
6. J. O'Leary, P. C. Bell, J. D. Wallis and W. B. Schweizer, J. Chem. Soc., Perkin Trans. 2, 2001, 133.
7. P. C. Bell, M. Drameh, N. Hanly and J. D. Wallis, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2000, C56, 670.
8. J. Clayden, C. McCarthy and M. Helliwell, Chem. Commun., 1999, 2059.
9. D. R. W. Hodgson, A. J. Kirby and N. Feeder, J. Chem. Soc., Perkin Trans. 1, 1999, 949.
10. A. C. Blackburn and R. E. Gerkin, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1997, C53, 1077.
11. J. C. Galluci, D. J. Hart and G. J. Young, Acta Crystallogr., Sect. B: Struct. Sci., 1998, B54, 73.
12. P. C. Bell, W. Skranc, X. Formosa, J. O'Leary and J. D. Wallis, J. Chem. Soc., Perkin Trans. 2, 2002, 878.
13. M. Parvez and I. I. Schuster, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1990, C46, 947;
14. G. Procter, D. Britton and J. D. Dunitz, Helv. Chim. Acta, 1981, 64, 471.
15. A. Panda, G. Mugesh, H. B. Singh and R. J. Butcher, Organometallics, 1999, 18, 1986.
16. C. Breliere, F. Carre, R. J. P. Corriu, M. Poirier and G. Royo, Organometallics, 1986, 5, 388;
17. F. Carre, G. Cerveau, C. Chuit, R. J. P. Corriu and C. Reye, New J. Chem., 1992, 16, 63;
18. C. Breliere, F. Carre, R. J. P. Corriu, W. E. Douglas, M. Poirier, G. Royo and M. W. C. Man, Organometallics, 1992, 11, 1586;
19. F. Carre, R. J. P. Corriu, A. Kpoton, M. Poirier, G. Royo, J. C. Young and C. Belin, J. Organomet. Chem., 1994, 470, 43.
20. C. Cox, H. Wack and T. Lectka, Angew. Chem., Int. Ed., 1999, 38, 798.
21. P. R. Mallison, G. T. Smith, C. C. Wilson, E. Grech and K. Wozniak, J. Am. Chem. Soc., 2003, 125, 4259;
22. K. Wozniak, P. R. Mallinson, G. T. Smith, C. C. Wilson and E. Grech, J. Phys. Org. Chem., 2003, 16, 764.
23. P. Hodgson, G. C. Lloyd-Jones, M. Murray, T. M. Peakman and R. L. Woodward, Chem. Eur. J., 2000, 6, 4451.
24. K. Akiba, M. Yamashita, Y. Yamamoto and S. Nagase, J. Am. Chem. Soc., 1999, 121, 10644;
25. M. Yamashita, Y. Yamamoto, K. Akiba, D. Hashizume, F. Iwasaki, N. Takagi and S. Nagase, J. Am. Chem. Soc., 2005, 127, 4354.
26. M. Yamashita, K. Kamura, Y. Yamamoto and K. Akiba, Chem. Eur. J., 2002, 8, 2976.
27. J. E. Davies, A. J. Kirby and I. V. Komarov, Helv. Chim. Acta, 2003, 86, 1222;
28. A. J. Kirby, I. V. Komarov, V. A. Bilenko, J. E. Davies and J. M. Rawson, Chem. Commun., 2002, 2106.
29. K. A. Lyssenko, S. M. Aldoshin and M. Y. Antipin, Mendeleev Commun., 2004, 98.
30. C. S. Frampton, H. Straver, J. D. Wallis and S. J. Coles, in preparation.
31. Cambridge Structural Database, F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci., 2002, B58, 380.
32. H. J. Wasserman, R. R. Ryan and S. P. Layne, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1985, C41, 783.
33. D. Hashizume, N. Miki, T. Yamazaki, Y. Aoyagi, T. Arisato, H. Uchiyama, T. Endo, M. Yasui and F. Iwasaki, Acta Crystallogr., Sect. B: Struct. Sci., 2003, B59, 404.
34. T. J. Kidd, T. J. A. Loontjens, D. A. Leigh and J. K. Y. Wong, Angew. Chem., Int. Ed., 2003, 42, 3379.
35. M. Iwata, H. Nagase, T. Endo and H. Ueda, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1997, C53, 329.
36. T. Koch and M. Hesse, Synthesis, 1995, 251.
37. O. Carugo, G. Poli and L. Manzoni, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1992, C48, 2013.
38. S.-G. Roh and J. H. Jeong, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 2000, C56, e529.
39. Nitro groups are attached to sp3 C atoms, structures measured at T ≤ 130 K.
40. M. Reetz, S. Hutte and F. Goddard, Z. Naturforsch., B: Chem. Sci., 1995, 50, 415.
41. M. Sievert, N. Nagel, H. Bock and R. Dienelt, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1999, C55, 1147.
42. T. D. Ladyzhnikova, A. G. Tyrkov, K. V. Altukhov, V. P. Pozdnyakov, M. O. Dekaprilevich and K. I. Rezchikova, Zh. Org. Khim, 1992, 28, 912.
43. P. Veya, C. Floriani, A. Chiesi-Villa and C. Guastini, Organometallics, 1991, 10, 1652;
44. P. Veya, C. Floriani, A. Chiesi-Villa and C. Rizzolo, Organometallics, 1994, 13, 214.
45. L. R. Favello, S. Hicke and T. E. Mueller, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1995, C51, 859.
46. H. Bock and N. Nagel, Z. Naturforsch., B: Chem. Sci., 1998, 53, 792.
47. The structure measured at higher temperature may show a very small apparent shortening of bonds due to the effects of thermal motion, but this should be rather small for these temperatures.
48. N. Nishiwaki, T. Nogami, C. Tanaka, F. Nakashima, Y. Inoue, N. Asaka, Y. Tohda and M. Ariga, J. Org. Chem., 1999, 64, 2160.
49. W. R. Bowman, B. T. Golding and W. P. Watson, J. Chem. Soc., Perkin Trans. 2, 1980, 731.
50. G. C. Lloyd-Jones, J. N. Harvey, P. Hodgson, M. Murray and R. L. Woodward, Chem. Eur. J., 2003, 9, 4523.
51. M. Pilkington, J. D. Wallis, G. T. Smith and J. A. K. Howard, J. Chem. Soc., Perkin Trans. 2, 1996, 1849;
52. G. T. Smith, J. A. K. Howard and J. D. Wallis, Phys. Chem. Chem. Phys., 2001, 3, 4501.
53. R. Glaser and C. Horan, Can. J. Chem., 1996, 74, 1200;
54. C. J. Horan, C. L. Barnes and R. Glaser, Chem. Ber., 1993, 126, 243;
55. C. J. Horan, C. L. Barnes and R. Glaser, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1993, C49, 507;
56. C. J. Horan, P. E. Haney, C. L. Barnes and R. Glaser, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1993, C49, 1525;
57. R. Glaser, C. J. Horan, E. D. Nelson and M. K. Hall, J. Org. Chem., 1992, 57, 215.
58. J. Z. Gougoutas, Cryst. Struct. Commun., 1982, 11, 1305;
59. J. Z. Gougoutas, Cryst. Struct. Commun., 1978, 7, 183;
60. J. Z. Gougoutas, J. Am. Chem. Soc., 1979, 101, 5672;
61. J. Z. Gougoutas and J. Johnson, J. Am. Chem. Soc., 1978, 100, 5816.
62. J. D. Wallis and J. D. Dunitz, Helv. Chim. Acta, 1993, 76, 1411.
63. C. P. Brock and J. D. Dunitz, Acta Crystallogr., B: Struct. Sci., 1982, B38, 2218.
64. A. J. Kirby and J. M. Percy, Tetrahedron, 1988, 44, 6903.
65. G. M. Sheldrick, SHELX-97, Program for refinement of crystal structures, University of Göttingen, Germany, 1997.
66. L. Farrugia, PLATON (A. L. Spek, University of Utrecht) for Windows, University of Glasgow, 2004.
67. C. K. Johnson and M. N. Burnett, ORTEPIII Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USA.
68. POVRAY, Persistence of Vision Ray Tracer graphics program, www.povray.org.