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Volumn 5, Issue 6, 1999, Pages 1785-1793

Kinetic and product studies on the side-chain fragmentation of 1-arylalkanol radical cations in aqueous solution: Oxygen versus carbon acidity

Author keywords

Alcohols; Cleavage reactions; Pulse radiolysis; Radical cations; Radical reactions

Indexed keywords

1 ARYL ALKANOL DERIVATIVE; ALCOHOL DERIVATIVE; CARBON; OXYGEN; RADICAL; UNCLASSIFIED DRUG;

EID: 0033017164     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990604)5:6<1785::AID-CHEM1785>3.0.CO;2-0     Document Type: Article
Times cited : (40)

References (69)
  • 19
    • 0001632942 scopus 로고
    • W. S. Trahanovsky, J. Cramer, J. Org. Chem. 1971, 36, 1890-1893; W. S. Trahanovsky, N. S. Fox, J. Am. Chem. Soc. 1974, 96, 7968-7974.
    • (1971) J. Org. Chem. , vol.36 , pp. 1890-1893
    • Trahanovsky, W.S.1    Cramer, J.2
  • 20
    • 0001092957 scopus 로고
    • W. S. Trahanovsky, J. Cramer, J. Org. Chem. 1971, 36, 1890-1893; W. S. Trahanovsky, N. S. Fox, J. Am. Chem. Soc. 1974, 96, 7968-7974.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7968-7974
    • Trahanovsky, W.S.1    Fox, N.S.2
  • 23
    • 85034534758 scopus 로고    scopus 로고
    • note
    • [16]
  • 26
    • 85034537893 scopus 로고    scopus 로고
    • note
    • [24] for the neutral parent compounds 5 and 11.
  • 29
    • 85034545381 scopus 로고    scopus 로고
    • note
    • - values are considered, since it is likely that in the transition state the resonance effect is more important than the inductive effect.
  • 36
    • 85034556104 scopus 로고    scopus 로고
    • note
    • 4CH•OH.
  • 38
    • 85034551615 scopus 로고    scopus 로고
    • note
    • [7]
  • 39
    • 85034530833 scopus 로고    scopus 로고
    • note
    • Alternatively, it is possible that, concerted with heterolytic C-C fragmentation (Scheme 2), the β-OH group is deprotonated, and that this process profits from the large hydration energy of the (incipient) proton.
  • 42
  • 46
    • 85034545476 scopus 로고    scopus 로고
    • note
    • a to about 12-13.
  • 48
    • 0347337287 scopus 로고
    • (Ed.: J. K. Kochi), Wiley, New York
    • K. U. Ingold, in Free Radicals, Vol. 1 (Ed.: J. K. Kochi), Wiley, New York, 1973, pp. 99-102.
    • (1973) Free Radicals, Vol. 1 , vol.1 , pp. 99-102
    • Ingold, K.U.1
  • 51
    • 36749108643 scopus 로고
    • S. Saebø, L. Radom, H. F. Schaefer, J. Chem. Phys. 1983, 78, 845-853; G. F. Adams, R. J. Bartlett, G. D. Purvis, Chem. Phys. Lett. 1982, 87, 311-314; C. Sosa, H. B. Schlegel, J. Am. Chem. Soc. 1987, 109, 7007-7015.
    • (1983) J. Chem. Phys. , vol.78 , pp. 845-853
    • Saebø, S.1    Radom, L.2    Schaefer, H.F.3
  • 52
    • 0010312747 scopus 로고
    • S. Saebø, L. Radom, H. F. Schaefer, J. Chem. Phys. 1983, 78, 845-853; G. F. Adams, R. J. Bartlett, G. D. Purvis, Chem. Phys. Lett. 1982, 87, 311-314; C. Sosa, H. B. Schlegel, J. Am. Chem. Soc. 1987, 109, 7007-7015.
    • (1982) Chem. Phys. Lett. , vol.87 , pp. 311-314
    • Adams, G.F.1    Bartlett, R.J.2    Purvis, G.D.3
  • 53
    • 33845281259 scopus 로고
    • S. Saebø, L. Radom, H. F. Schaefer, J. Chem. Phys. 1983, 78, 845-853; G. F. Adams, R. J. Bartlett, G. D. Purvis, Chem. Phys. Lett. 1982, 87, 311-314; C. Sosa, H. B. Schlegel, J. Am. Chem. Soc. 1987, 109, 7007-7015.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7007-7015
    • Sosa, C.1    Schlegel, H.B.2
  • 54
    • 33751157530 scopus 로고
    • RN1 Mechanism, ACS Monograph, 1983, 178, chapter 6; A. B. Pierini, J. S. Duca, Jr., J. Chem. Soc. Perkin Trans. 2 1995, 1821-1828.
    • (1994) J. Phys. Chem. , vol.98 , pp. 3716-3724
    • Savéant, J.-M.1
  • 55
    • 0027968145 scopus 로고
    • RN1 Mechanism, ACS Monograph, 1983, 178, chapter 6; A. B. Pierini, J. S. Duca, Jr., J. Chem. Soc. Perkin Trans. 2 1995, 1821-1828.
    • (1994) Tetrahedron , vol.50 , pp. 10117-10165
    • Savéant, J.-M.1
  • 56
    • 0003279562 scopus 로고
    • RN1 mechanism
    • chapter 6
    • RN1 Mechanism, ACS Monograph, 1983, 178, chapter 6; A. B. Pierini, J. S. Duca, Jr., J. Chem. Soc. Perkin Trans. 2 1995, 1821-1828.
    • (1983) ACS Monograph , vol.178
    • Rossi, R.A.1    De Rossi, R.H.2
  • 58
    • 85034539095 scopus 로고    scopus 로고
    • note
    • Note that the present case refers to a radical zwitterion rather than to a radical cation.
  • 61
    • 0001951530 scopus 로고    scopus 로고
    • In line with this hypothesis are the results of semi-empirical calculations on 3,4-dimethoxybenzyl alcohol radical cation, which show that the alcoholic H atom bears much more positive charge than the benzylic H atoms: T. Elder, Holzforschung 1997, 51, 47-56.
    • (1997) Holzforschung , vol.51 , pp. 47-56
    • Elder, T.1
  • 62
    • 33947306589 scopus 로고
    • R. A. Marcus, J. Phys. Chem. 1968, 72, 891-899; A. O. Cohen, R. A. Marcus, J. Phys. Chem. 1968, 72, 4249-4256.
    • (1968) J. Phys. Chem. , vol.72 , pp. 891-899
    • Marcus, R.A.1
  • 63
    • 0012818340 scopus 로고
    • R. A. Marcus, J. Phys. Chem. 1968, 72, 891-899; A. O. Cohen, R. A. Marcus, J. Phys. Chem. 1968, 72, 4249-4256.
    • (1968) J. Phys. Chem. , vol.72 , pp. 4249-4256
    • Cohen, A.O.1    Marcus, R.A.2


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