A dynamic model of reaction pathway effects on parahydrogen-induced nuclear spin polarization

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8677-8683

  Buntkowsky, Gerd ^a   Bargon, Joachim ^b   Limbach, Hans Heinrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CALCULATION; DRUG STRUCTURE; MOLECULAR DYNAMICS; TECHNIQUE;

EID: 0029848832     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954188b     Document Type: Article

References (57)

1. Osborn. J. A.; Jardine, F. H;. Young, J. F.; Wilkonson, G. J. J. Chem. Soc. A 1966, 1711.
2. Brown, J. M.; Evans, P. ; Lucy, A. R. J. Chem. Soc., Perkin Trans 2 1987, 1591.
3. (a) Bowers, C. R.; Weitekamp, D. P. Phys. Rev. Lett. 1986, 57, 2645.
4. (b) Pravica, M. G.; Weitekamp, D. P. Chem. Phys. Lett. 1988, 145, 255.
5. (c) Bowers, C. R.; Weitekamp, D. P. J. Am. Chem. Soc. 1987, 109, 554.
6. (d) Bowers, C. R.; Jones, D. H.; Kurur, N. D.; Labinger, J. A.; Pravica, M. G.; Weitekamp, D. P. Adv. Magn. Reson. 1990, 15, 269.
7. (a) Silvera, I. F. Rev. Mod. Phys. 1980, 52, 393.
8. (b) van Kranendonk, J. Solid Hydrogen; Plenum: New York, 1983.
9. (c) Abragam, A. The Principles of Nuclear Magnetism; Clarendon Press: Oxford, 1961.
10. (a) Eisenschmidt, T. C.; Kirss, R. U.; Deutsch, P. P.; Hommeltoft, S. I.; Eisenberg, R.; Bargon, J. J. Am. Chem. Soc. 1987, 109, 8089.
11. (b) Kirss, R. U;. Eisenschmidt, T.; Eisenberg, R. J. Am. Chem. Soc., 1988, 110, 8564.
12. (c) Eisenberg, R. Acc. Chem. Res. 1991, 24, 110.
13. (a) Bargon, J.; Kandels, J.; Woelk, K. Z. Phys. Chem. 1993, 180, 65.
14. (b) Kating, P.; Wandelt, A.; Selke, R.; Bargon, J. J. Phys. Chem. 1993, 97, 13313.
15. (c) Bargon, J.; Kandels, J.; Kating, P. J. Chem. Phys. 1993, 98, 6150.
16. (d) Bargon, J.; Kandels, J.; Kating, P.; Thomas, A.; Woelk, K. Tetrahedron Lett. 1990, 31, 5721.
17. (e) Bargon, J.; Kandels, J.; Woelk, K. Angew. Chem. 1990, 102, 70; Angew. Chem., Int. Ed. Engl. 1990, 29, 58.
18. (e) Bargon, J.; Kandels, J.; Woelk, K. Angew. Chem. 1990, 102, 70; Angew. Chem., Int. Ed. Engl. 1990, 29, 58.
19. (a) Kubas, G. J. ; Ryan, R. R.; Swanson, B. I.; Vergamini, P. J.; Wasserman, H. J. J. Am. Chem. Soc. 1984, 106, 451.
20. (b) Kubas, G. J. Acc. Chem. Res. 1988, 21, 120.
21. (c) Rattan, G.; Kubas, G. J.; Unkefer, C. J.; Van Der Sluys, L. S.; Kubat-Martin, K. A. J. Am. Chem. Soc. 1990, 112, 3855.
22. (d) Eckert, J. ; Kubas, G. J. J. Phys. Chem. 1993, 97, 2378.
23. Crabtree, R. H. Acc. Chem. Res. 1990, 23, 95.
24. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
25. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
26. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
27. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
28. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
29. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
30. 3 were discussed by Labinger, J. A. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon Press: New York, 1983; Vol. 3, p 707, cited as unpublished results of F. N. Tebbe. (b) Arliguie, T. ; Chaudret, B. ; Devillers, J. ; Poilblanc, R. C. R. Acad. Sci., Ser. 11 1987, 305, 1523. (c) Antinolo, A.; Chaudret, B.; Commenges, G.; Fajardo, M.; Jalon, F.; Morris, R. H.; Otero, A.; Schweitzer, C. T. J. Chem. Soc., Chem. Commun. 1988, 1210. (d) Arliguie, T.; Border, C. Chaudret, B.; Devilles, J.; Poilblanc, R. Organometallics 1989, 8, 1308. (e) Arliguie, T.; Chaudret, B.; Jalon, F. A.; Otero, A.; Lopez, J. A.; Lahoz, F. J. Organometallics 1991, 10, 1888. (f) Chaudret, B.; Limbach, H. H.; Moise, C. C. R. Acad. Sci., Ser. 11, 1992, 315, 533. (g) Sabo-Étienne, S.; Chaudret, B.; Abou el Makarim, H.; Barthelat, J. C.; Daudey, J. P.; Ulrich, S.; Limbach, H. H.; Moise, C. J. Am. Chem. Soc. 1995, 117, 11602.
31. Paciello, R. R.; Manriquez, J. M.; Bercaw, J. E. Organometallics 1990, 9, 260.
32. Heinekey, D. M.; Payne, N. G.; Schulte, G. K. J. Am. Chem. Soc. 1988, 110, 2303.
33. (a) Heinekey, D. M.; Millar, J. M.; Koetzle, T. F.; Payne, N. G.; Zilm, K. W. J. Am. Chem. Soc. 1990, 112, 909.
34. (b) Zilm, K. W.; Heinekey, D. M.; Millar, J. M.; Payne, N. G.; Demou, P. J. Am. Chem. Soc. 1989, 111, 3088.
35. (c) Zilm, K. W.; Heinekey, D. M. ; Millar, J. M.; Payne, N. G.; Neshyba, S. P.; Duchamp, J. C.; Szczyrba, J. J. Am. Chem. Soc. 1990, 112, 920.
36. (d) Zilm, K. W.; Millar, J. M. Adv. Magn. Reson. 1990, 15, 163.
37. (e) Inati, S. J.; Zilm, K. W. Phys. Rev. Lett. 1992, 68, 3273.
38. (f) Wisniewski, L. L.; Mediati, M.; Jensen, C. M.; Zilm, K. W. J. Am. Chem. Soc. 1993, 115, 7534.
39. Jones, D.; Labinger, J. A.; Weitekamp, J. J. Am. Chem. Soc. 1989, 111, 3087.
40. (a) Limbach, H. H.; Scherer, G.; Maurer, M.; Chaudret, B. Angew. Chem. 1992, 104, 1414; Angew. Chem., Int. Ed. Engl. 1990, 31, 1369.
41. (a) Limbach, H. H.; Scherer, G.; Maurer, M.; Chaudret, B. Angew. Chem. 1992, 104, 1414; Angew. Chem., Int. Ed. Engl. 1990, 31, 1369.
42. (b) Limbach, H. H.; Ulrich, S.; Buntkowsky, G.; Sabo-Étienne, S.; Chaudret, B.; Kubas, G. J.; Eckert, J. Submitted for publication.
43. Barthelat, J. C.; Chaudret, B.; Dauday, J. P.; De Loth, Ph.; Poilblanc, R. J. Am. Chem. Soc. 1991, 113, 9896.
44. Jarid, A.; Moreno, M.; Lled¢s. A.; Lluch, J. M.; Bertran, J. J. Am. Chem. Soc., 1993, 115, 5861.
45. (a) Hiller, E. M.; Harris, R. A. J. Chem. Phys. 1993, 98, 2077.
46. (b) Ibid. 1993, 99, 7652.
47. (c) Ibid. 1993, 100, 2522.
48. Szymanski, S. J. Mol. Struct. 1994, 321, 115.
49. Binsch, G. J. Am. Chem. Soc. 1969, 91, 1304.
50. Emsley, J. W.; Feeney, J.; Sutcliffe, L. H. High Resolution NMR Spectroscopy; Pergamon Press: Oxford, 1965; Vol. 1.
51. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of NMR in One and Two Dimensions; Clarendon Press: Oxford, 1987.
52. Limbach, H. H. Dynamic NMR Spectroscopy in the Presence of Kinetic Hydrogen Deuterium Isotope Effects. NMR Basic Principles and Progress; Berlin, Heidelberg, New York, 1991; Chapter 2.
53. (a) Moler, C. B.; Van Loan, C. F. Siam Rev. 1978, 20, 801.
54. (b) Golub, G. H.; Van Loan, C. F. Matrix Computation; John Hopkins University Press: Baltimore, 1983, Chapter 11.
55. LAPACK Program package, University of California, Berkeley, 1994, distributed by AT&T Laboratories New Jersey. E-mail address: netlib@research.att.com.
56. Haake, M.; Barkemeyer, J.; Bargon, J. J. Phys. Chem. 1995, 99, 17539. Haake, M.; Barkemeyer, J.; Bargon, J. Unpublished results.
57. Haake, M.; Barkemeyer, J.; Bargon, J. J. Phys. Chem. 1995, 99, 17539. Haake, M.; Barkemeyer, J.; Bargon, J. Unpublished results.