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Volumn , Issue 14, 2008, Pages 2463-2472

Thermodynamic study of σH complexes in nucleophilic aromatic substitution reactions: Relative stabilities of electrochemically generated radicals

Author keywords

H complexes; Aromatic substitution; Electrochemistry; Nucleophilic substitution; Oxidation; Reaction mechanisms

Indexed keywords


EID: 53749102454     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701098     Document Type: Article
Times cited : (15)

References (51)
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    • b) I. Gallardo, G. Guirado, J. Marquet, patent pending ES2000/489;
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    • For compound 3, see: F. Millot, F. Terrier, Bull. Soc. Chim. Fr. 1971, 11, 3897;
    • a) For compound 3, see: F. Millot, F. Terrier, Bull. Soc. Chim. Fr. 1971, 11, 3897;
  • 21
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    • for compound 4, see: C. F. Bernasconi, J. Am. Chem. Soc. 1970, 92, 4682;
    • b) for compound 4, see: C. F. Bernasconi, J. Am. Chem. Soc. 1970, 92, 4682;
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    • for compound 5, see: M. R. Crampton, J. A. Stevens, J. Chem. Soc. Perkin Trans. 2 1991, 7, 925;
    • c) for compound 5, see: M. R. Crampton, J. A. Stevens, J. Chem. Soc. Perkin Trans. 2 1991, 7, 925;
  • 23
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    • for compound 6, see: J. H. Clark, M. S. Robertson, A. Cook, C. Streich, J. Flourine Chem. 1985, 28, 161;
    • d) for compound 6, see: J. H. Clark, M. S. Robertson, A. Cook, C. Streich, J. Flourine Chem. 1985, 28, 161;
  • 24
    • 53749087100 scopus 로고    scopus 로고
    • for compound 7, see: M. P. Egorov, G. A. Artamkina, I. P. Beletskaya, O. A. Reutov, Izves. Akadem. Nauk SSSR, Ser. Chim. 1978, 10, 2431;
    • e) for compound 7, see: M. P. Egorov, G. A. Artamkina, I. P. Beletskaya, O. A. Reutov, Izves. Akadem. Nauk SSSR, Ser. Chim. 1978, 10, 2431;
  • 25
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    • for compound 8, see: E. Buncel, N. Chuaqui-Offermanns, R. Y. Moir, R. A. Norris, Can. J. Chem. 1979, 57, 494.
    • f) for compound 8, see: E. Buncel, N. Chuaqui-Offermanns, R. Y. Moir, R. A. Norris, Can. J. Chem. 1979, 57, 494.
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    • Electrochemical Reactions in Investigation of Rates and Mechanism of Reactions
    • Ed, C. F. Bernasconi, Wiley, New York, chapter 2.1;
    • a) C. P. Andrieux, J.-M. Savéant, Electrochemical Reactions in Investigation of Rates and Mechanism of Reactions in Techniques of Chemistry, vol. 6 (Ed.: C. F. Bernasconi), Wiley, New York, 1986, chapter 2.1;
    • (1986) Techniques of Chemistry , vol.6
    • Andrieux, C.P.1    Savéant, J.-M.2
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    • simulations were performed by using DIGISIM software, commercially available from BAS Corp
    • c) simulations were performed by using DIGISIM software, commercially available from BAS Corp.
  • 38
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    • The differences between the peak potential and standard oxidation potential[6,7] in the case of σH complexes is 0.03 V (ca. 1 kcalmol-1, whereas in the case of σX complexes it is 0.08 V ca. 2 kcalmol-1, Thus, these differences would not introduce significant uncertainties into the determined values of ΔG°;
    • -1). Thus, these differences would not introduce significant uncertainties into the determined values of ΔG°;


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