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Volumn 62, Issue 19, 1997, Pages 6539-6546

σ,π Interaction in Halogen-Substituted Biadamantylidene Radical Cations

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Indexed keywords


EID: 0000180939     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970252r     Document Type: Article
Times cited : (18)

References (73)
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    • Techniques of Chemistry, Weinberg, N. L., Ed.; Wiley: New York
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    • (b) Parker, V. D.; J. Am. Chem. Soc. 1976, 98, 98. Clar, E.; Schmidt, W. Tetrahedron 1975, 33, 2093; 1977, 35, 1027. Schmidt, W. J. Phys. Chem. 1966, 66, 828.
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    • (b) Parker, V. D.; J. Am. Chem. Soc. 1976, 98, 98. Clar, E.; Schmidt, W. Tetrahedron 1975, 33, 2093; 1977, 35, 1027. Schmidt, W. J. Phys. Chem. 1966, 66, 828.
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    • (b) Parker, V. D.; J. Am. Chem. Soc. 1976, 98, 98. Clar, E.; Schmidt, W. Tetrahedron 1975, 33, 2093; 1977, 35, 1027. Schmidt, W. J. Phys. Chem. 1966, 66, 828.
    • (1977) Tetrahedron , vol.35 , pp. 1027
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    • (b) Parker, V. D.; J. Am. Chem. Soc. 1976, 98, 98. Clar, E.; Schmidt, W. Tetrahedron 1975, 33, 2093; 1977, 35, 1027. Schmidt, W. J. Phys. Chem. 1966, 66, 828.
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    • Schmidt, W.1
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    • note
    • F, p 291, ref 8b, and include all the substituents used) the average deviation for all 15 vIP values is 0.05 eV, and 10(OH), which has the most powerful resonance group, is 0.07 eV harder to ionize than the regression predicts, instead of being easier. The worst deviator is 10(I), 0.14 eV easier to ionize, and 10(Br) is 0.06 eV easier to ionize than the regression predicts. As shown in Table 2, 10(Br) is 2.1 kcal/mol easier to oxidize than 10(Cl), which is also the wrong direction for a resonance effect.
  • 53
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    • p 209 for the plot, p 227 for discussion
    • (b) Topsom, R. D. Prog. Phys. Org. Chem. 1987, 16, 193 (p 209 for the plot, p 227 for discussion).
    • (1987) Prog. Phys. Org. Chem. , vol.16 , pp. 193
    • Topsom, R.D.1
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    • Reference 1c, footnote 15
    • Reference 1c, footnote 15.
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    • note
    • 12b The point that using any reasonable drop-off does not make an additive two-pathway δ-substituted system have a larger effect than a γ-substituted system is not changed.
  • 60
    • 0000534393 scopus 로고
    • (c) For recent application in fullerene radical spectra, see Percivcal, P. W.; Wlodek, S, Chem. Phys. Lett. 1992, 196, 317. Borghi, R.; Lunazzi, V.; Placucci, G.; Krusic, P. J.; Dixon, D. A.; Matsuzawa, N.; Masafumi, A. J. Am. Chem. Soc. 1996, 118, 7608.
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    • Percivcal, P.W.1    Wlodek, S.2
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    • (d) Roth recently argued that there was a logical error in deriving the Whiffen effect [Roth, H. D.; Lakkaraju, P. S. J. Phys. Chem. 1993, 97, 13403], but as Williams has pointed out, these arguments are not correct [Williams, F. J. Phys. Chem. 1994, 98, 8258].
    • (1993) J. Phys. Chem. , vol.97 , pp. 13403
    • Roth, H.D.1    Lakkaraju, P.S.2
  • 63
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    • (d) Roth recently argued that there was a logical error in deriving the Whiffen effect [Roth, H. D.; Lakkaraju, P. S. J. Phys. Chem. 1993, 97, 13403], but as Williams has pointed out, these arguments are not correct [Williams, F. J. Phys. Chem. 1994, 98, 8258].
    • (1994) J. Phys. Chem. , vol.98 , pp. 8258
    • Williams, F.1
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    • note
    • +,Cl̇ formation.
  • 71
    • 85178351670 scopus 로고    scopus 로고
    • note
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.