Thermodynamics of Inter-and Intramolecular Hydrogen Bonding in (Diphosphine)platinum(II) Diolate Complexes and Its Role in Carbohydrate Complexation Regioselectivity

Inorganic Chemistry

Volumn 36, Issue 25, 1997, Pages 5832-5844

  Andrews, Mark A ^a,b   Cook, Gerald K ^a   Shriver, Zachary H ^a  

^a BROOKHAVEN NATIONAL LABORATORY   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383180     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970860p     Document Type: Article

References (70)

1. Andrews, M. A.; Voss, E. J.; Gould, G. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 5730-5740.
2. Appelt, A.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1988, 938-940.
3. Klooster, W. T.; Voss, E. J.; Andrews, M. A.; Koetzle, T. F. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, March 13-17, 1994; American Chemical Society: Washington, DC, 1994; INOR 292.
4. For a recent comprehensive summary, see: Kapteijn, G. M.; Dervisi, A.; Grove, D. M.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 10939-10949 and references therein.
5. Cook, G. K.; Andrews, M. A. J. Am. Chem. Soc. 1996, 118, 9448-9449.
6. Whitfield, D. M.; Stojkovski, S.; Sarkar, B. Coord. Chem. Rev. 1993, 122, 171-225.
7. Angyal, S. J. Adv. Carbohydr. Chem. Biochem. 1989, 47, 1-43.
8. Yano, S. Coord. Chem. Rev. 1988, 92, 113-156.
9. Burger, J.; Klüfers, P. Chem. Ber. 1995, 128, 75-79 and references therein.
10. Chapelle, S.; Sauvage, J. P.; Verchere, J. F. Inorg. Chem. 1994, 33, 1966-1971 and references therein.
11. Bilik, V. S., L. Chem. Zvesti 1973, 27, 544-546.
12. Hayes, M. L.; Pennings, N. J.; Serianni, A. S.; Barker, R. J. Am. Chem. Soc. 1982, 104, 6764-6769 and references therein.
13. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes; 2nd ed.; Wiley: New York, 1992.
14. Murthy, A. S. N.; Rao, C. N. R. Appl. Spectrosc. Rev. 1968, 2, 69-191.
15. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker, Inc.: New York, 1974.
16. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
17. Gramstad, T.; Becker, E. D. J. Mol. Struct. 1970, 5, 253-261.
18. Aksnes, G.; Gramstad, T. Acta Chem. Scand. 1960, 14, 1485-1494.
19. Cook, G. K. Unpublished observations.
20. Pimentel, G. C.; McClellan, A. L. Annu. Rev. Phys. Chem. 1971, 22, 347-385.
21. Tucker, E. E.; Lippert, E. In The Hydrogen Bond Recent Developments in Theory and Experiments. II. Structure and Spectroscopy; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland Publishing Co.: New York, 1976; Vol. II, pp 793-830.
22. Joesten, M. D. J. Chem. Educ. 1982, 59, 362-366.
23. Hadzi, D.; Bratos, S. In The Hydrogen Bond. Recent Developments in Theory and Experiments. II. Structure and Spectroscopy; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland Publishing Co.: New York, 1976; Vol. II, pp 567-611.
24. Sherry, A. D. In The Hydrogen Bond: Recent Developments in Theory and Experiments. III. Dynamics, Thermodynamics and Special Systems; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland Publishing Co.: New York, 1976; Vol. III, pp 1201-1224.
25. Wiley, G. R.; Miller, S. I. J. Am. Chem. Soc. 1972, 94, 3287-3293.
26. Scatchard, G. Ann. N.Y. Acad. Sci. 1949, 51, 660.
27. Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565.
28. Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104.
29. Osakada, K.; Kim, Y.-J.; Yamamoto, A. J. Organomet. Chem. 1990, 383, 303-317.
30. Alsters, P. L.; Baesjou, P. J.; Janssen, M. D.; Kooijman, H.; Sicherer-Roetman, A.; Spek, A. L.; van Koten, G. Organometallics 1992, 11, 4124-4135.
31. Kapteijn, G. M.; Dervisi, A.; Grove, D. M.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 10939-10949.
32. Osakada, K.; Kim, Y.-J.; Tanaka, M.; Ishiguro, S.-i.; Yamamoto, A. Inorg. Chem. 1991, 30, 197-200.
33. Deranleau, D. A. J. Am. Chem. Soc. 1969, 91, 4044-4049.
34. Deranleau, D. A. J. Am. Chem. Soc. 1969, 91, 4050-4054.
35. Abelbeck Software, distributed by Synergy Software, 2457 Perkiomen Ave., Reading, PA 19606.
36. The Math Works, Inc., 24 Prime Park Way, Natick, MA 01760.
37. Voss, E. J.; Brunkan, N. M. Unpublished observations.
38. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383.
39. HB values at 273 and 323 K given in ref 18).
40. Compare study of solvent dependence of hydrogen bonding between phenol and pyridine: Spencer, J. N.; Andrefsky, J. C.; Grushow, A.; Naghdi, J.; Patti, L. M.; Trader, J. F. J. Phys. Chem. 1987, 91, 1673-1674.
41. Joris, L.; Mitsky, J.; Taft, R. W. J. Am. Chem. Soc. 1972, 94, 3438-3442.
42. Gurka, D.; Taft, R. W. J. Am. Chem. Soc. 1969, 91, 4794-4801.
43. Compare similar results for multiple hydrogen bonding in o-hydroxyl-substituted benzoic acids: Shan, S.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515-5518.
44. 3.
45. 2.
46. See ref 15, pp 247-251.
47. Tichy, M. Adv. Org. Chem. 1965, 5, 115-290.
48. Aaron, H. S. Top. Stereochem. 1979, 11, 1-52.
49. See: Beeson, C.; Pham, N.; Shipps, G. J.; Dix, T. A. J. Am. Chem. Soc. 1993, 115, 6803-6812 and references therein for recent studies.
50. Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1994, 116, 3892-3900.
51. Tse, Y.-C.; Newton, M. D.; Allen, L. C. Chem. Phys. Lett. 1980, 75, 350-356.
52. Schuster, P. In The Hydrogen Bond. Recent Developments in Theory and Experiments. I. Theory of the Hydrogen Bond; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland Publishing Co.: New York, 1976; Vol. I, p 123 ff.
53. Dziembowska, T.; Szczodrowska, B.; Krygowski, T. M.; Grabowski, S. J. J. Phys. Org. Chem. 1994, 7, 142-146.
54. Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444-1456.
55. Olovsson, I.; Jönsson, P.-G. In The Hydrogen Bond Recent Developments in Theory and Experiments. II. Structure and Spectrospcopy; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland: New York, 1976; Vol. II, pp 393-456.
56. Perkampus, H. H.; Miligy, F.; Kerim, A. Spectrochim. Acta 1968, 244, 2071-2079.
57. Kulevsky, N.; Lewis, L. J. Phys. Chem. 1972, 76, 3502-3503.
58. Prabhumirashi, L. S. J. Chem. Soc., Faraday Trans. 2 1978, 74, 1567-1572 and prior work cited therein.
59. IR studies have also been reported for α,ω-diols (Busfield, W. K.; Ennis, M. P.; McEwen, I. J. Spectrochim. Acta 1973, 29A, 1259-1264) and 4-(hydroxymethyl)-1,3-dioxolanes (Aksnes, G.; Albriktsen, P. Acta Chem. Scand. 1966, 20, 1330-1334), but these suffer from flawed experimental protocols such as assuming equal extinction coefficients for free and hydrogen bonded hydroxyls or temperature independence of the extinction coefficients.
60. IR studies have also been reported for α,ω-diols (Busfield, W. K.; Ennis, M. P.; McEwen, I. J. Spectrochim. Acta 1973, 29A, 1259-1264) and 4-(hydroxymethyl)-1,3-dioxolanes (Aksnes, G.; Albriktsen, P. Acta Chem. Scand. 1966, 20, 1330-1334), but these suffer from flawed experimental protocols such as assuming equal extinction coefficients for free and hydrogen bonded hydroxyls or temperature independence of the extinction coefficients.
61. Calculated from data in ref 57.
62. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
63. Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: New York, 1988.
64. Hayashi, H.; Nakanishi, K.; Brandon, C.; Marmur, J. J. Am. Chem. Soc. 1973, 95, 8749-8757.
65. Kelly, J. W.; Evans, S. A. J. J. Am. Chem. Soc. 1986, 108, 7681-7685.
66. Van Geet, A. L. Anal. Chem. 1970, 42, 679-680.
67. Aldrich Catalog Handbook of Fine Chemicals; Aldrich Chemical Co., Milwaukee, WI, 1994-1995.
68. From the Design Institute for Physical Property Data (DIPPR) file, American Institute of Chemical Engineers (AIChe) accessed via the Scientific and Technical Information Network (STN).
69. Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805-4813.
70. Hodgman, C. D. In Mathemetical Tables, 10th ed.; Hodgman, C. D., Ed.; Chemical Rubber Publishing Co.: Cleveland, OH, 1954; p 295.