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Volumn 73, Issue 2, 2008, Pages 618-629

One-electron oxidation of 2-(4-methoxyphenyl)-2-methylpropanoic and 1-(4-methoxyphenyl)cyclopropanecarboxylic acids in aqueous solution. The involvement of radical cations and the influence of structural effects and pH on the side-chain fragmentation reactivity

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANECARBOXYLIC ACIDS; SIDE-CHAIN FRAGMENTATION;

EID: 41149121645     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702104j     Document Type: Article
Times cited : (6)

References (94)
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    • See for example: a
    • See for example: (a) Cleland, W. W. Acc. Chem. Res. 1999, 32, 862-868.
    • (1999) Acc. Chem. Res , vol.32 , pp. 862-868
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    • This notation represents an oversimplification because, as compared to the radical cations, the corresponding radical zwitterions lack the presence of the carboxylic proton
    • This notation represents an oversimplification because, as compared to the radical cations, the corresponding radical zwitterions lack the presence of the carboxylic proton.
  • 52
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    • It is important to point out that the time-resolution of the LFP equipment used in this study (8 ns laser pulse) is significantly higher than that of the PR equipment (300 ns electron pulse).
    • It is important to point out that the time-resolution of the LFP equipment used in this study (8 ns laser pulse) is significantly higher than that of the PR equipment (300 ns electron pulse).
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    • Bally, T.; Borden, W. T. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; Wiley-VCH: New York, 1999; Vol. 13, pp 1-97.
    • (1999) Reviews in Computational Chemistry , vol.13 , pp. 1-97
    • Bally, T.1    Borden, W.T.2
  • 62
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    • An analogous situation has been described previously for the SO 4•--induced oxidation of 4-methylphenyl- and 4-methoxyphenylethanoic acids in aqueous solution see ref 14a
    • •--induced oxidation of 4-methylphenyl- and 4-methoxyphenylethanoic acids in aqueous solution (see ref 14a).
  • 64
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    • •-.
    • •-.
  • 68
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    • 58
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    • -1.
    • -1.
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    • 62: sweep rates 100 mV/s). All values are in V vs SCE in acetonitrile.
    • 62: sweep rates 100 mV/s). All values are in V vs SCE in acetonitrile.
  • 77
    • 41149092452 scopus 로고    scopus 로고
    • In ref 62, the value of the standard oxidation potential for cumene is given in trifluoroacetic acid (TFA) as 2.29 V vs SCE. The value of 2.17 V vs SCE in acetonitrile derives from the application of the corrective factor previously determined for the oxidation potentials of alkylbenzenes E°MeCN, E°TFA, 0.12 V, 65
    • 65
  • 81
    • 41149097606 scopus 로고    scopus 로고
    • Also the adiabatic ionization potentials that can be obtained on the basis of the computed energy differences between the most stable structures of 2•+ and 2 and of 3•+ and 3 (7.48 and 7.33 eV, respectively, see the Supporting Information) point in this direction
    • •+ and 3 (7.48 and 7.33 eV, respectively, see the Supporting Information) point in this direction.
  • 83
    • 41149122146 scopus 로고    scopus 로고
    • -1 reported above, and confirms that the 4-metoxycumyl radical is more stable than the 1-(4-methoxyphenyl)cyclopropyl radical. (Chemical Equation Presented)
    • -1 reported above, and confirms that the 4-metoxycumyl radical is more stable than the 1-(4-methoxyphenyl)cyclopropyl radical. (Chemical Equation Presented)
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.