Hydrolysis of (2-deoxy-α-D-glucopyranosyl)pyridinium salts: The 2- deoxyglucosyl oxocarbenium is not solvent-equilibrated in water

Journal of the American Chemical Society

Volumn 120, Issue 16, 1998, Pages 3887-3893

  Zhu, Jiang ^a   Bennet, Andrew J ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CONFORMATIONAL TRANSITION; HYDROLYSIS; REACTION ANALYSIS; SOLVATION;

EID: 0032577021     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973945y     Document Type: Article

References (47)

1. For example, see: Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83-105. Richard, J. P. Tetrahedron 1995, 51, 1535-1573.
2. For example, see: Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83-105. Richard, J. P. Tetrahedron 1995, 51, 1535-1573.
3. For some recent examples, see: Liras, J. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1997, 119, 8191-8200. Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1996, 118, 10371-10379. Jagannadham, V.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1993, 115, 8465-8466.
4. For some recent examples, see: Liras, J. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1997, 119, 8191-8200. Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1996, 118, 10371-10379. Jagannadham, V.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1993, 115, 8465-8466.
5. For some recent examples, see: Liras, J. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1997, 119, 8191-8200. Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1996, 118, 10371-10379. Jagannadham, V.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1993, 115, 8465-8466.
6. Capon, B. Chem. Rev. 1969, 69, 407-498.
7. Bennet, A. J.; Sinnott, M. L. J. Am. Chem. Soc. 1986, 108, 7287-7294.
8. Huang, X.; Surry, C.; Hiebert, T.; Bennet, A. J. J. Am. Chem. Soc. 1995, 117, 10614-10621.
9. Guthrie, R. D. Commission on Physical Organic Chemistry, IUPAC J. Pure Appl. Chem. 1989, 61, 23-56. Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.
10. Guthrie, R. D. Commission on Physical Organic Chemistry, IUPAC J. Pure Appl. Chem. 1989, 61, 23-56. Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.
11. Perrin, C. L.; Engler, R. E. J. Am. Chem. Soc. 1997, 119, 585-591.
12. Sinnott, M. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 2026-2032.
13. Buckley, N. Oppenheimer, N. J. J. Org. Chem. 1996, 61, 8039-8047.
14. Buckley, N. Oppenheimer, N. J. J. Org. Chem. 1996, 61, 8048-8062.
15. Edmundson, R. S. Tetrahedron 1965, 21, 2379-2387.
16. Initial kinetic measurements on 4d were performed with a sample that contained about 4% of the β-anomer (1). However, since the rate of hydrolysis for 1 is approximately 9-fold less than that of 4d (ref 5), following four-half-times for hydrolysis of 4d, approximately 1% of the total hydrolyzed material originated from 1.
17. (a) Lemieux, R. U.; Morgan A. R. Can. J. Chem. 1965, 43, 2205-2213.
18. (b) Hosie, L.; Marshall, P. J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1984, 1121-1131.
19. Swain, C. G.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 141-147. Ibne-Rase, K. M. J. Chem. Educ. 1967, 44, 89-94. Koivurinta, J.; Kyllönen, A.; Leononen, L.; Valaste, K.; Koskikallio, J. Finn. Chem. Lett. 1974, 239-243.
20. Swain, C. G.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 141-147. Ibne-Rase, K. M. J. Chem. Educ. 1967, 44, 89-94. Koivurinta, J.; Kyllönen, A.; Leononen, L.; Valaste, K.; Koskikallio, J. Finn. Chem. Lett. 1974, 239-243.
21. Swain, C. G.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 141-147. Ibne-Rase, K. M. J. Chem. Educ. 1967, 44, 89-94. Koivurinta, J.; Kyllönen, A.; Leononen, L.; Valaste, K.; Koskikallio, J. Finn. Chem. Lett. 1974, 239-243.
22. 16 from the total time of the reaction.
23. Wilkinson, F. Chemical Kinetics and Reaction Mechanisms; Van Nostrand Reinhold: New York, 1980; p 17.
24. 5
25. Bock, K.; Pedersen, C. Adv. Carbohyd. Chem. Biochem. 1983, 41, 27-66.
26. Perrin, D. D. Dissociation Constants of Organic Bases in Aqueous Solution; Butterworth: London, 1965.
27. Rounded to nearest 5%.
28. 3, Cl, and Br, respectively, whereas the corresponding ratios for α-D-xylopyranosyl 4′-bromoisoquinolinium bromide (80°C) are 2.03, 1.95, 2.17, 1.54, and 1.50 (ref 4).
29. Amyes, T. L.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7888-7900.
30. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7951-7958.
31. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1-19.
32. Giese, K.; Kaatze, U.; Pottel, R. J. Phys. Chem. 1970, 74, 3718-3725. Kaatze, U. J. Chem. Eng. Data 1989, 34, 371-374. Kaatze, U.; Pottel, R.; Schumacher, A. J. Phys. Chem. 1992, 96, 6017-6020.
33. Giese, K.; Kaatze, U.; Pottel, R. J. Phys. Chem. 1970, 74, 3718-3725. Kaatze, U. J. Chem. Eng. Data 1989, 34, 371-374. Kaatze, U.; Pottel, R.; Schumacher, A. J. Phys. Chem. 1992, 96, 6017-6020.
34. Giese, K.; Kaatze, U.; Pottel, R. J. Phys. Chem. 1970, 74, 3718-3725. Kaatze, U. J. Chem. Eng. Data 1989, 34, 371-374. Kaatze, U.; Pottel, R.; Schumacher, A. J. Phys. Chem. 1992, 96, 6017-6020.
35. form(acetate) = 1.25.
36. ipc.
37. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689-4691. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361-1372. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465.
38. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689-4691. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361-1372. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465.
39. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689-4691. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361-1372. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465.
40. Only shown are the data where the introduction of a second anion does not effect the quantity of retained azide formed, specifically shown are the three points: (1) 1.98 M azide; (2) 0.99 M azide containing 0.99 M acetate; and (3) 0.99 M azide containing 0.99 M fluoride.
41. -1.
42. Melander, L.; Saunders: W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience, New York-Chichester-Brisbane-Toronto, 1980; pp 235-248.
43. Huang, X.; Tanaka, K. E. S.; Bennet, A. J. J. Am. Chem. Soc. 1997, 119, 11147-11154.
44. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7958-7963.
45. Zhang, Y.; Bommuswamy, J.; Sinnott, M. L. J. Am. Chem. Soc. 1994, 116, 7557-7563.
46. Bennet, A. J.; Davis, A. J.; Hosie, L.; Sinnott, M. L. J. Chem. Soc., Perkin Trans 2 1987, 581-584.
47. Rosenberg, S.; Kirsch, J. F. Biochemistry 1981, 20, 3196-3204.