Change of rate limiting step in general acid-catalyzed benzo[a]pyrene diol epoxide hydrolysis

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4327-4333

  Lin, Bin ^a   Islam, Nafisa ^a   Friedman, Steve ^a   Yagi, H ^b   Jerina, Donald M ^b   Whalen, Dale L ^a  

^a UNIVERSITY OF MARYLAND   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,8 DIHYDROXYBENZO[A]PYRENE 9,10 OXIDE; ACID; AMMONIA; BUFFER; CATION; DIOXANE DERIVATIVE; SODIUM AZIDE; SOLVENT; TROMETAMOL; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; HYDROLYSIS; PH; PKA;

EID: 0032513721     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972982m     Document Type: Article

References (33)

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16. 6
17. The cis and trans prefixes for tetrols 3 and azidohydrins 6 refer to the relative stereochemistry of the C-9 and C-10 groups.
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20. Facile general base-catalyzed addition of solvent to a number of carbocations has been established: (a) Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 4966. (b) Ritchie, C. D. Acc. Chem. Res. 1972, 5, 348. (c) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1396.
21. Facile general base-catalyzed addition of solvent to a number of carbocations has been established: (a) Ritchie, C. D.; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 4966. (b) Ritchie, C. D. Acc. Chem. Res. 1972, 5, 348. (c) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1396.
22. 0.
23. A change in rate-limiting step with change in pH and buffer concentrations has been observed in the solvolysis of precocene I oxide: Sayer, J. M.; Grossman, S. J.; Adusei-Poku, K. S.; Jerina, D. M. J. Am. Chem. Soc. 1988, 110, 5068.
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28. s ratios similar to that for 1 have been proposed to occur at the diffusion-controlled limit: (a) Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361. (b) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689. (c) TaSha, R.; Rappoport, Z. Ibid. 1983, 105, 6082.
29. s ratios similar to that for 1 have been proposed to occur at the diffusion-controlled limit: (a) Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361. (b) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689. (c) TaSha, R.; Rappoport, Z. Ibid. 1983, 105, 6082.
30. s ratios similar to that for 1 have been proposed to occur at the diffusion-controlled limit: (a) Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1361. (b) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 4689. (c) TaSha, R.; Rappoport, Z. Ibid. 1983, 105, 6082.
31. -1, ref 8).
32. a for an α-hydroxycarbocation isomeric with 1 is estimated to be ca. 13, ref 8.
33. For a summary of requirements for concerted general acid catalysis, see: Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 4731.