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Volumn 121, Issue 9, 1999, Pages 1826-1833

α-(acyloxy)dialkylnitrosamines: Effects of structure on the formation of N-nitrosiminium ions and a predicted change in mechanism

Author keywords

[No Author keywords available]

Indexed keywords

NITROSAMINE;

EID: 0033541159     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9833218     Document Type: Article
Times cited : (14)

References (47)
  • 1
    • 0345218894 scopus 로고
    • Chemical Carcinogens; Searle, C. D., Ed.; American Chemical Society, Washington, DC
    • Lawley, P. D. In Chemical Carcinogens; Searle, C. D., Ed.; ACS Monograph 182; American Chemical Society, Washington, DC, 1984.
    • (1984) ACS Monograph , vol.182
    • Lawley, P.D.1
  • 5
    • 0039429271 scopus 로고
    • Anselme, J.-P., Ed.; American Chemical Society: Washington, DC
    • Wiessler, M. In N-Nitrosamines; Anselme, J.-P., Ed.; American Chemical Society: Washington, DC, 1979; p 57.
    • (1979) N-Nitrosamines , pp. 57
    • Wiessler, M.1
  • 12
    • 0000594594 scopus 로고
    • Karabatsos, G. J.; Vane, F. M.; Taller, R. A.; Hsi, N. J. Am. Chem. Soc. 1964, 86, 3351. Karabatsos, G. L.; Taller, R. A. J. Am. Chem. Soc. 1964, 86, 4373.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 4373
    • Karabatsos, G.L.1    Taller, R.A.2
  • 16
    • 0038836584 scopus 로고
    • Doyle, M. P.; Wierenga, W.; Zaleta, M. A. J. Org. Chem. 1972, 37, 1597. Dovle, M. P.; Zaleta, M. A.; DeBoer, J. E.; Wierenga, W. J. Org. Chem. 1973, 38, 1963.
    • (1972) J. Org. Chem. , vol.37 , pp. 1597
    • Doyle, M.P.1    Wierenga, W.2    Zaleta, M.A.3
  • 18
    • 0345650694 scopus 로고    scopus 로고
    • note
    • A scheme and details on the method of calculation are included in the Supporting Information.
  • 19
    • 0344788026 scopus 로고    scopus 로고
    • note
    • A value of p* = - 1.50 was published on the basis of three substituents in ref 6.
  • 20
    • 0344788025 scopus 로고    scopus 로고
    • note
    • 1g of -1.09.
  • 25
    • 0004233459 scopus 로고
    • Secondary and Solvent Isotope Effects; Buncel, E.; Lee. C. C., Eds.; Elsevier: New York
    • Westaway, K. C. In Isotopes in Organic Chemistry, Vol. 7; Secondary and Solvent Isotope Effects; Buncel, E.; Lee. C. C., Eds.; Elsevier: New York, 1987.
    • (1987) Isotopes in Organic Chemistry , vol.7
    • Westaway, K.C.1
  • 26
    • 0000484720 scopus 로고
    • Kresge, A. J.; Weeks, D. P. J. Am. Chem. Soc. 1984, 106, 7140. Shiner, V. J.; Cross, S. J. Am. Chem. Soc. 1957, 79, 3599. Shiner, V. J. Tetrahedron 1959 5, 243.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7140
    • Kresge, A.J.1    Weeks, D.P.2
  • 27
    • 0002729275 scopus 로고
    • Kresge, A. J.; Weeks, D. P. J. Am. Chem. Soc. 1984, 106, 7140. Shiner, V. J.; Cross, S. J. Am. Chem. Soc. 1957, 79, 3599. Shiner, V. J. Tetrahedron 1959 5, 243.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 3599
    • Shiner, V.J.1    Cross, S.2
  • 28
    • 0001446191 scopus 로고
    • Kresge, A. J.; Weeks, D. P. J. Am. Chem. Soc. 1984, 106, 7140. Shiner, V. J.; Cross, S. J. Am. Chem. Soc. 1957, 79, 3599. Shiner, V. J. Tetrahedron 1959 5, 243.
    • (1959) Tetrahedron , vol.5 , pp. 243
    • Shiner, V.J.1
  • 37
    • 0342370439 scopus 로고    scopus 로고
    • Exner, O.; Bohm, S. J. Chem. Soc., Perkin Trans. 2 1997, 1235. Clyde, E.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1977, 678. But see: Cooney, B. T., Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 1235
    • Exner, O.1    Bohm, S.2
  • 38
    • 37049099836 scopus 로고
    • Exner, O.; Bohm, S. J. Chem. Soc., Perkin Trans. 2 1997, 1235. Clyde, E.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1977, 678. But see: Cooney, B. T., Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1977) J. Chem. Soc., Perkin Trans. 2 , pp. 678
    • Clyde, E.1    Taylor, R.2
  • 39
    • 84970601802 scopus 로고
    • Exner, O.; Bohm, S. J. Chem. Soc., Perkin Trans. 2 1997, 1235. Clyde, E.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1977, 678. But see: Cooney, B. T., Happer, D. A. R. Aust. J. Chem. 1987, 40, 1537.
    • (1987) Aust. J. Chem. , vol.40 , pp. 1537
    • Cooney, B.T.1    Happer, D.A.R.2
  • 40
    • 33947090266 scopus 로고
    • Radom, L.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1972, 94, 5935. Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. v. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221. Wiersehke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5935
    • Radom, L.1    Pople, J.A.2    Schleyer, P.V.R.3
  • 41
    • 33947088922 scopus 로고
    • Radom, L.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1972, 94, 5935. Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. v. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221. Wiersehke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6221
    • Hoffmann, R.1    Radom, L.2    Pople, J.A.3    Schleyer, P.V.R.4    Hehre, W.J.5    Salem, L.6
  • 42
    • 0022026522 scopus 로고
    • Radom, L.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1972, 94, 5935. Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. v. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221. Wiersehke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1496
    • Wiersehke, S.G.1    Chandrasekhar, J.2    Jorgensen, W.L.3
  • 43
    • 33845183013 scopus 로고
    • Radom, L.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1972, 94, 5935. Hoffmann, R.; Radom, L.; Pople, J. A.; Schleyer, P. v. R.; Hehre, W. J.; Salem, L. J. Am. Chem. Soc. 1972, 94, 6221. Wiersehke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 819
    • Ibrahim, M.R.1    Jorgensen, W.L.2
  • 45
    • 0344788023 scopus 로고    scopus 로고
    • note
    • 2 substituent has a single hydrogen atom that can stabilize the developing carbocation by hyperconjugation while those in Figure 3 have two; however, this means that the rate constant for 33 actually deviates by more than +3 log units from the appropriate correlation.


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