15N NMR study of proton localization and proton transfer thermodynamics and kinetics in polycrystalline porphycene

Journal of Physical Organic Chemistry

Volumn 13, Issue 1, 2000, Pages 23-34

  Langer, Uwe ^a   Hoelger, Christof ^a,d   Wehrle, Bernd ^a,e   Latanowicz, Lidia ^b   Vogel, Emanuel ^c   Limbach, Hans Heinrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b PEDAGOGICAL UNIVERSITY   (Poland)

^c UNIVERSITY OF COLOGNE   (Germany)

^d BEIERSDORF AG   (Germany)

^e BAYER AG   (Germany)

Author keywords

15N NMR; Kinetics; Polycrystalline porphycene; Proton localization; Proton transfer; Thermodynamics

Indexed keywords

EID: 0002107442     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(200001)13:1<23::AID-POC211>3.0.CO;2-W     Document Type: Article

References (67)

1. Elguero J, Marzin C, Katrizky AR, Linda P. The Tautomerism of Heterocycles. Academic Press: New York, 1976 (the 2nd edition of this book will appear in 2000).
2. (a) Baldy A, Elguero J, Faure R, Pierrot M, Vincent EJ. J. Am. Chem. Soc. 1985; 107: 5290;
3. (b) Smith JAS, Wehrle B, Aguilar-Parrilla F, Limbach HH, Foces-Foces MC, Cano FH, Elguero J, Baldy A, Pierrot M. Khurshid MMT, Larcombe-McDouall JB. J. Am. Chem. Soc. 1989; 111, 7304;
4. (c) Aguillar-Parrilla F, Limbach HH, Blanz M, Rayner TJ, Smith JAS. Magn. Reson. Relat. Phenom. 1990; 25, 615;
5. (d) Aguilar-Parrilla F, Cativiela C, Diaz de Villegas MD, Elguero J, Foces-Foces MC, Laureiro JIG, Cano FH, Limbach HH, Smith JAS, Toiron C. J. Chem. Soc., Perkin Trans. 2 1992; 1737;
6. (f) Aguilar-Parrilla F, Scherer G, Limbach HH, Foces-Foces MC, Cano FH, Smith JAS, Toiron C, Elguero J. J. Am. Chem. Soc. 1992; 114, 9657;
7. (g) Toda F, Tanaka K, Foces-Foces MC, Llamas-Saiz AL, Limbach HH, Aguilar-Parrilla F, Claramunt RM, Lopez C, Elguero J. J. Chem. Soc., Chem. Commun. 1993; 1139;
8. (h) Aguilar-Parrilla F, Claramunt RM, Lopez C, Sanz D, Limbach HH, Elguero J. J. Phys. Chem. 1994; 98, 8752;
9. (i) Elguero J, Cano FH, Foces-Foces MC, Llamas-Saiz AL, Limbach HH, Aguilar-Parrilla F, Claramunt RM, Lopez C. J. Heterocycl. Chem. 1994; 31, 695;
10. (j) Aguilar-Parrilla F, Männle F, Limbach HH, Elguero J, Jagerovic N. Magn. Reson. Chem. 1994; 32, 699;
11. (k) Lamas-Saiz AL, Foces-Foces MC, Cano FH, Elguero J, Jimenez P, Laynez J, Meutermans W, Elguero J, Limbach HH, Aguilar-Parrilla F. Acta Crystallogr., Sect. B 1994; 50, 746;
12. (l) Aguilar-Parrilla F, Limbach HH, Foces-Foces MC, Cano FH, Jagerovic N, Elguero J. J. Org. Chem. 1995; 60, 1965;
13. (m) Elguero J, Jagerovic N, Foces-Foces MC, Cano FH, Roux MV, Aguilar-Parrilla F, Limbach HH. J. Heterocycl. Chem. 1995; 32, 451;
14. (n) Hoelger CG, Limbach HH, Aguilar-Parrilla F, Elguéro J, Weintraub O, Vega S. J. Magn. Reson. A 1996; 120, 46;
15. (o) Lopez C, Claramunt RM, Llamas-Saiz A, Foces-Foces MC, Elguero J, Sobrados I, Aguilar-Parrilla F, Limbach HH. New J. Chem. 1996; 20, 523;
16. (p) de Paz JLG, Elguero J, Foces-Foces MC, Llamas-Saiz A, Aguilar-Parrilla F, Klein O, Limbach HH. J. Chem. Soc., Perkin Trans. 2 1997; 101;
17. (q) Aguilar-Parrilla F, Klein O, Elguero J, Limbach HH. Ber. Bunsenges. Phys. Chem. 1997; 101, 884;
18. (r) Anulewicz R, Wawer I, Krygowski TM, Männle F, Limbach H-H. J. Am. Chem. Soc. 1997; 119, 12223;
19. (s) Männle F, Wawer I, Limbach HH. Chem. Phys. Lett. 1996; 256, 657.
20. (a) Limbach HH, Hennig J, Kendrick RD, Yannoni CS. J. Am. Chem. Soc. 1984; 106: 4059;
21. (b) Wehrle B, Limbach HH, Köcher M, Ermer O, Vogel E. Angew. Chem., 1987; 99: 914; Angew. Chem., Int. Ed. Engl. 1987; 26: 934;
22. (b) Wehrle B, Limbach HH, Köcher M, Ermer O, Vogel E. Angew. Chem., 1987; 99: 914; Angew. Chem., Int. Ed. Engl. 1987; 26: 934;
23. (c) Wehrle B, Limbach HH. Chem. Phys. 1989; 136: 223;
24. (d) Braun J, Schlabach M, Wehrle B, Köcher M, Vogel E and Limbach HH. J. Am. Chem. Soc. 1994; 116: 6593;
25. (e) Braun J, Limbach HH, Williams P, Morimoto H, Wemmer D. J. Am. Chem. Soc. 1996; 30: 7231;
26. (f) Braun J, Schwesinger R, Williams PG, Morimoto H, Wemmer DE, Limbach HH. J. Am. Chem. Soc. 1996; 118: 11101;
27. (g) Frydman B, Fernandez CO, Vogel E. J. Org. Chem. 1998; 63: 9835.
28. (a) Limbach HH, Wehrle B. Zimmermann H, Kendrick R, Yannoni CS. Angew. Chem. 1987; 99: 241; Angew. Chem., Int. Ed. Engl. 1987; 26: 247;
29. (a) Limbach HH, Wehrle B. Zimmermann H, Kendrick R, Yannoni CS. Angew. Chem. 1987; 99: 241; Angew. Chem., Int. Ed. Engl. 1987; 26: 247;
30. (b) Limbach HH, Wehrle B, Zimmermann H, Kendrick R, Yannoni CS. J. Am. Chem. Soc. 1987; 109: 929;
31. (c) Wehrle B, Zimmermann H, Limbach HH. J. Am. Chem. Soc. 1988; 110: 7014;
32. (d) Wehrle B, Aguilar-Parrilla F, Limbach HH. J. Magn. Reson. 1990; 87: 584;
33. (e) Aguilar-Parrilla F, Wehrle B, Bräunling H, Limbach HH. J. Magn. Reson. 1990; 87: 592;
34. (f) Benedict C, Langer U, Limbach HH, Ogata H, Takeda S. Ber. Bunsenges. Phys. Chem. 1998; 102: 335.
35. Limbach HH, Wehrle B, Schlabach M, Kendrick R, Yannoni CS. J. Magn. Reson., 1988; 77: 84.
36. Hoelger CG, Wehrle B, Benedict H, Limbach HH. J. Phys. Chem. 1994; 98: 843.
37. Vogel E, Köcher M, Schmickler H, Lex J. Angew. Chem. 1986; 98: 262; Angew. Chem., Int. Ed. Engl. 1986; 26: 257.
38. Vogel E, Köcher M, Schmickler H, Lex J. Angew. Chem. 1986; 98: 262; Angew. Chem., Int. Ed. Engl. 1986; 26: 257.
39. Rumpel H, Limbach HH. J. Am. Chem. Soc., 1989; 111: 5429.
40. (a) Maisch K, Hohlneicher G. J. Phys. Chem. A 1997; 101: 8409;
41. (b) Galievsky V, Starukhin A, Vogel E, Waluk J. J. Phys. Chem. A 1998; 102: 4966.
42. Starukhin A, Vogel E, Waluk J. J. Phys. Chem. A 1998; 102: 9999.
43. Bell RP. The Tunnel Effect, Chapman and Hall, London 1980.
44. Torchia DAJ. Magn. Reson. 30: 613 (1978).
45. Du Bois Murphy P. J. Magn. Reson., 1986; 70: 307.
46. 15
47. (a) Witanowski M, Stefaniak L, Szymanski S, Januszewski H. J. Magn. Reson. 1977; 28: 217;
48. (b) Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B;
49. (c) Martin G, Martin ML, Gouesnard JP. NMR - Basic Principles and Progress, vol. 18. Springer: Heidelberg, 1989;
50. (d) Srinivasan PR, Lichter RL. J. Magn. Reson. 1977; 28: 227.
51. (a) Andrew ER, Latanowicz L. J. Magn. Reson. 1986; 68: 232;
52. (b) Latanowicz L, Reynhardt EC. Ber. Bunsenges. Phys. Chem. 1994; 98: 818;
53. (c) Latanowicz L, Reynhardt EC, Utrecht R, Medycki W. Ber. Bunsenges. Phys. Chem. 1995; 99: 152;
54. (d) Reynhardt EC, Latanowicz L. Chem. Phys. Lett., 1996; 251: 235;
55. (e) Takeda S, Inabe T, Benedict C, Langer U, Limbach HH. Ber. Bunsenges. Phys. Chem. 1998; 102: 1358.
56. (a) Scherer G, Limbach HH. J. Am. Chem. Soc. 1989; 111: 5946;
57. (b) Scherer G, Limbach HH. J. Am. Chem. Soc. 1994; 116: 1230;
58. (c) Scherer G, Limbach HH. Croat. Chem. Acta 1994; 67: 431.
59. (a) Steiner Th, W. Saenger W. Acta Crystallogr., Sect. B 1994; 50: 348;
60. (b) Steiner Th. J. Chem. Soc., Chem. Commun. 1995; 1331;
61. (c) Gilli P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 1994; 116: 909.
62. Benedict H, Limbach HH, Wehlan M, Fehlhammer WP, Golubev NS, Janoschek R. J. Am. Chem. Soc. 1998; 120: 2939.
63. (a) Webb LE, Fleischer EB. J. Chem. Phys. 1965; 43: 3100;
64. (b) Chen BML, Tulinsky A. J. Am. Chem. Soc. 1972; 94: 4144;
65. (c) Hennig J, Limbach HH. J. Am. Chem. Soc., 1984; 106: 292.
66. Hennig J, Limbach HH. J. Am. Chem. Soc. 1984; 106: 292.
67. Smirnov SN, Benedict H, Golubev NS, Denisov GS, Kreevoy MM, Schowen RL, Limbach HH. Can J. Chem. 1999; 77: 943.