Combined X-ray diffraction and 15N CPMAS NMR study of molecular structure and proton order/disorder phenomena in cyclic N,N'- bisarylformamidine dimers

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12223-12230

  Anulewicz, Romana ^a   Wawer, Iwona ^b   Krygowski, Tadeusz Marek ^a   Männle, Ferdinand ^c   Limbach, Hans Heinrich ^c  

^a UNIVERSITY OF WARSAW   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; FORMAMIDINE;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; X RAY DIFFRACTION;

EID: 0031576695     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970699h     Document Type: Article

References (60)

1. (a) Häfelinger, G. in The Chemistry of Amidines and Imidates; Patai, S., Ed.; Wiley: London, 1975; Vol. 1, Chapter 1, p 1.
2. Borisov, D. N.; Kratsov, D. N.; Peregudov, A. S.; Fedin, E. I. Izv. Akad. Nauk. SSSR, Ser. Khim. 1980, 2151.
3. (a) Meschede, L.; Gerritzen, D.; Limbach, H.-H. Ber. Bunsen-Ges. Phys. Chem. 1988, 92, 5669.
4. (b) Limbach, H.-H.; Meschede, L.; Scherer, G. Z. Naturforsch. 1989, 44a, 459.
5. (c) Meschede L.; Limbach, H.-H. J. Phys. Chem. 1991, 95, 10267 and references cited therein.
6. (a) Raczynska, E. D.; Laurence Ch. Analyst 1992, 117, 375.
7. (b) Anulewicz R.; Krygowski, T. M.; Raczynska, E. D. J. Phys. Org. Chem. 1991, 331.
8. Krygowski, T. M.; Wozniak, K. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, Chapter 2, p 101.
9. (a) Krajewski, J.; Urbanczyk-Lipkowska, Z.; Gluzinski, P.; Oszczapowicz, J.; Busko-Oszczapowicz, I.; Bleidelis, J.; Kemme, A. Pol. J. Chem. 1981, 55, 1015.
10. (b) Norrestam, R.; Mertz, S.; Grassland, I. Acta Crystallogr. 1983, C39, 1554.
11. (c) Norrestam, R. Acta Crystallogr. 1948, C40, 955. Gilli, G.; Bertolasi, V. J. Am. Chem. Soc. 1979, 101, 7704.
12. (c) Norrestam, R. Acta Crystallogr. 1948, C40, 955. Gilli, G.; Bertolasi, V. J. Am. Chem. Soc. 1979, 101, 7704.
13. (d) Kosturkiewicz, Z.; Ciszak, E.; Tykarska, E. Acta Crystallogr. 1992, B48 471.
14. Anulewicz, R.; Krygowski, T. M.; Pniewska. B., J. Cryst. Spectrosc. Res. 1987, 17, 661.
15. Anulewicz, R.; Krygowski, T. M.; Jaroszewska-Manaj, J.; Pniewska, B. Pol. J. Chem. 1991, 65, 465.
16. Anulewicz, R.; Krygowski, T. M.; Pniewska, B. Acta Crystallogr. 1990, C46, 2121.
17. Trueblood, K. N. In Accurate Molecular Structures, Their Determination and Importance; Domenicano, A., Hargittai, I., Eds.; Oxford University Press: 1992; Chapter 8, p 200.
18. (a) Meier, B. H.; Graf, F.; Ernst, R. R. J. Chem. Phys. 1982, 76, 768.
19. (b) Meyer, R.; Ernst, R. R. J. Chem. Phys. 1990, 93, 768.
20. (c) Heuer, A.; Haeberlen, U. J. Chem. Phys. 1991, 95, 4201.
21. (d) Stöckli, A.; Maier, B. H.; Kreis, R.; Meyer, R.; Ernst, R. R. J. Chem. Phys. 1990, 93, 15002.
22. (a) Smith, J. A. S.; Wehrle, F.; Aguilar-Parilla, F.; Limbach, H.-H.; Foces-Foces, M. C.; Cano, F. H.; Elguero, J.; Baldy, A.; Pierrot, M.; Khurshid M. M. T.; Lacombe-McDual, J. B. J. Am. Chem. Soc. 1989, 111, 7304.
23. (b) Aguilar-Parilla, F.; Scherer, G.; Limbach, H.-H.; Foces-Foces, M. C.; Cano, F. H.; Smith, J. A. S.; Toiron, C. Elguero, J. J. J. Am. Chem. Soc. 1992, 114, 9657.
24. (c) Aguilar-Parrilla, F.; Cativiela, C.; Diaz de Villegas, M. D.; Elguero, J.; Foces-Foces, C.; Laureiro, J. I. G.; Cano, F. H.; Limbach, H.-H.; Smith, J. A. S.; Toiron, C. J. Chem. Soc., Perkin Trans. 2 1992, 1737.
25. (d) Elguero, J.; Cano, F. H.; Foces-Foces, C.; Llamas-Saiz, A. L.; Limbach H.-H.; Aguilar-Parrilla, F.; Claramunt, R. M.; Lopez, C. J. Heterocycl. Chem. 1994, 31, 695.
26. (e) Aguilar-Parrilla, F.; Limbach, H.-H.; Foces-Foces, C.; Cano, F. H.; Jagerovic, N.; Elguero, J. J. Org. Chem. 1995, 60, 1965.
27. (f) Elguero, J.; Jagerovic, N.; Foces-Foces, C.; Cano, F. H.; Roux, M. V.; Aguilar-Parrilla, F.; Limbach, H.-H. J. Heterocycl. Chem. 1995, 32, 451.
28. (a) Limbach, H.-H.; Hennig, J.; Kendrick, R. D.; Yannoni, C. S. J. Am Chem. Soc. 1984, 106, 4059.
29. (b) Kendrick, R. D.; Friedrich, S.; Wehrle, B.; Limbach, H.-H.; Yannoni, C. S. J. Magn. Reson. 1985, 30, 159.
30. (c) Wehrle, B.; Limbach, H.-H.; Köcher, M.; Ermer, O.; Vogel, E. Angew. Chem. 1987, 99, 914; Angew. Chem. Int. Ed. Engl. 1987, 26, 934.
31. (c) Wehrle, B.; Limbach, H.-H.; Köcher, M.; Ermer, O.; Vogel, E. Angew. Chem. 1987, 99, 914; Angew. Chem. Int. Ed. Engl. 1987, 26, 934.
32. (d) Limbach, H.-H.; Wehrle, B.; Zimmermann, H.; Kendrick, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1987, 109, 929.
33. (e) Limbach, H.-H.; Wehrle, B.; Zimmermann, H.; Kendrick, R. D.; Yannoni, C. S. Angew. Chem. 1987, 99, 241; Angew. Chem., Int. Ed. Engl. 1987, 26, 247.
34. (e) Limbach, H.-H.; Wehrle, B.; Zimmermann, H.; Kendrick, R. D.; Yannoni, C. S. Angew. Chem. 1987, 99, 241; Angew. Chem., Int. Ed. Engl. 1987, 26, 247.
35. (f) Wehrle, B.; Limbach, H.-H.; Zimmermann, H. Ber. Bunsen-Ges. Phys. Chem. 1987, 91, 941.
36. (g) Limbach, H.-H.; Wehrle, B.; Schlabach, M.; Kendrick, R. D.; Yannoni, C. S. J. Magn. Reson. 1988, 77, 84.
37. (h) Wehrle, B.; Zimmermann, H.; Limbach, H.-H. J. Am. Chem. Soc. 1988, 110, 7014.
38. (i) Wehrle, B.; Limbach, H.-H. Chem. Phys., 1989, 136, 223.
39. (j) Schlabach, M.; Wehrle, B.; Braun, J., Scherer, G.; Limbach, H.-H. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 821.
40. (k) Braun, J.; Schlabach, M.; Wehrle, B.; Köcher, M.; Vogel, E.; Limbach, H.-H. J. Am. Chem. Soc. 1994, 116, 6593.
41. (l) Hoelger, C. G.; Wehrle, B.; Benedict, H.; Limbach, H.-H. J. Phys. Chem. 1994, 98, 843.
42. Limbach, H.-H. In NMR Basic Principles and Progress, Vol. 23: Deuterium and Shift Calculation: Springer-Verlag Heidelberg, 1991; Chapter 2, pp 66-167.
43. Limbach, H.-H.; Scherer G.; Meschede, L.; Aguilar-Parrilla, F.; Wehrle, B.; Braun, J.; Hoelger, Ch.; Benedict, H.; Buntkowsky, G.; Fehlhammer, W. P.; Elguero, J.; Smith, J. A. S.; Chaudret, B. NMR studies of Elementary Steps of Hydrogen Transfer in Condensed Phases. In Ultrafast Reaction, Dynamics and Solvent Effects, Experimental Aspects; Gaudel, Y., Rossky, P. J., Eds.; American Institute of Physics: Woodbury, NY, 1993.
44. Männle F.; Wawer I.; Limbach H. H. Chem. Phys. Lett. 1996, 256, 667.
45. Grout, R. J. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; Wiley: New York, Chichester, 1975; Chapter 6 and references cited therein.
46. Claisen, L. Liebigs Ann. 1895, 287, 366.
47. Lambert, J. B.; Stec, D., III Org. Magn. Reson. 1984, 22, 301.
48. Ott, D. G. Synthesis with stable isotopes of C, N, and O; Wiley: New York, 1981.
49. Axenrod, T.; Pregosin, P. S.; Wieder, M. J.; Becker, E. D.; Bradley, R. B.; Milne, G. W. A. J. Am. Chem. Soc. 1971, 93, 6536.
50. Aguilar-Parrilla, F.; Männle, F.; Limbach, H.-H.; Elguero, J.; Jagerovic, N. Magn. Reson. Chem. 1994, 32, 699.
51. Walker, J.; Stuart, J. Acta Crystallogr. 1983, A39, 158.
52. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
53. Sheldrick, G. M. SHELXL93. Program for Refinement of Crystal Structure; University of Göttingen: Germany, 1993.
54. (a) Rumpel, H.; Limbach, H.-H.; Zachmann, G. J. Phvs. Chem. 1989, 93, 1812.
55. (b) Rumpel, H.; Limbach, H.-H. J. Am. Chem. Soc. 1989, 111, 5429.
56. Männle, F.; Limbach, H.-H. Angew. Chem. 1996, 108, 477-479; Angew. Chem., Int. Ed. Engl. 1996, 35, 441.
57. Männle, F.; Limbach, H.-H. Angew. Chem. 1996, 108, 477-479; Angew. Chem., Int. Ed. Engl. 1996, 35, 441.
58. Bent, H. A. Chem. Rev. 1961, 61, 275.
59. Wozniak, K.; Krygowski, T. M.; Kariuki, B.; Jones, W. J. Mol. Struct. 1991, 248, 331.
60. Anulewicz, R., Acta Crystallogr. 1997, C53, 345.