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Volumn 71, Issue 21, 2006, Pages 8028-8036

Abstraction of iodine from aromatic iodides by alkyl radicals: Steric and electronic effects

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION; HARTREE FOCK (HF); RADICAL ABSTRACTION; STRAIN ENERGY;

EID: 33750012026     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061125a     Document Type: Conference Paper
Times cited : (22)

References (72)
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    • note
    • Deleted in press.
  • 4
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    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • (b) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
    • (2001) Radicals in Organic Synthesis
  • 24
    • 33749984951 scopus 로고    scopus 로고
    • note
    • -1 with MPW1K/LACV3P**.
  • 25
    • 33749986186 scopus 로고    scopus 로고
    • note
    • 12 by assuming that log A for the reaction is 8.5. The activation energy for the abstraction of iodine is expected to be somewhat lower.
  • 29
    • 33750000264 scopus 로고    scopus 로고
    • note
    • 10,14-16
  • 33
    • 33750011386 scopus 로고    scopus 로고
    • note
    • 4.
  • 34
    • 33749990784 scopus 로고    scopus 로고
    • note
    • The values of log A for a series of structurally similar compounds presented in Table 1 differ from one another to the extent of 0.6 (except for the compound 10, for which a higher value is most probably a consequence of an experimental uncertainty). Such a change in log A amounts to a factor of 4 in the rate constant, which is much smaller than differences in the measured rate constants. However, slightly lower values of log A can be found for sterically more hindered compounds, which is in agreement with the expectations.
  • 41
    • 33749999721 scopus 로고    scopus 로고
    • note
    • 3.
  • 48
    • 33749988978 scopus 로고    scopus 로고
    • note
    • The computed reaction energies for the abstraction of iodine from various iodobenzenes by cyclohexyl radicals exhibit a general trend which is in reverse proportionality with computed steric energies.
  • 50
    • 33750020805 scopus 로고    scopus 로고
    • note
    • s = O (Figure 1), and log A = 8.5 (Table 1).
  • 56
    • 0002297186 scopus 로고
    • Hypervalent halogen compounds
    • Patai, S., Rappoport, Z., Eds, Wiley: Chichester, U.K.
    • (b) Koser, G. F. Hypervalent Halogen Compounds. In The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds, Wiley: Chichester, U.K., 1983.
    • (1983) The Chemistry of Functional Groups, Supplement D
    • Koser, G.F.1
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    • 33749998858 scopus 로고    scopus 로고
    • Akiba, K.-y., Ed.; Wiley-VCH: New York
    • (c) Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999.
    • (1999)
    • Compounds, C.O.H.1
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    • 33750030405 scopus 로고    scopus 로고
    • note
    • Spectroscopically pure compound (NMR, elemental analysis) exhibits an unusually broad melting range, measured on various instruments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.