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Volumn 68, Issue 9, 2003, Pages 3433-3438

Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph•) in alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; HYDROGEN BONDS; IONIZATION; PHENOLS; RATE CONSTANTS;

EID: 0037414534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026917t     Document Type: Article
Times cited : (394)

References (39)
  • 1
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    • (a) Blois, M. S. Nature 1958, 181, 1199-1200.
    • (1958) Nature , vol.181 , pp. 1199-1200
    • Blois, M.S.1
  • 2
    • 0242513277 scopus 로고    scopus 로고
    • Note
    • For the period 1999 to 2001-end, Chemical Abstracts (SciFinder) lists 468 papers with the word pair diphenylpicrylhydrazyl and antioxidants.
  • 6
    • 0242573194 scopus 로고
    • Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, subvolume c
    • (d) For a comprehensive listing of rate constants for the reactions of dpph• with phenols to 1982, see: Ingold, K. U. In Landolt-Börnstein, New Series, Group II, Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, 1983; Vol. 13, subvolume c. In the next decade no kinetic measurements on these reactions were reported (!), see: Ingold, K. U.; Walton, J. C. In Landolt-Börnstein, New Series, Group II, Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, 1994; Vol. 18, subvolume c.
    • (1983) Landolt-Börnstein New Series Group II Radical Reaction Rates in Liquids , vol.13
    • Ingold, K.U.1
  • 7
    • 0242573194 scopus 로고
    • Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, subvolume c
    • (d) For a comprehensive listing of rate constants for the reactions of dpph• with phenols to 1982, see: Ingold, K. U. In Landolt-Börnstein, New Series, Group II, Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, 1983; Vol. 13, subvolume c. In the next decade no kinetic measurements on these reactions were reported (!), see: Ingold, K. U.; Walton, J. C. In Landolt-Börnstein, New Series, Group II, Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, Germany, 1994; Vol. 18, subvolume c.
    • (1994) Landolt-Börnstein, New Series, Group II, Radical Reaction Rates in Liquids , vol.18
    • Ingold, K.U.1    Walton, J.C.2
  • 25
    • 0003669158 scopus 로고
    • Serjeant, E. P., Dempsey, B., Eds.; IUPAC Chemical Data Series, No. 23; Pergamon Press: Oxford, UK
    • Ionisation constants of organic acids in aqueous solution; Serjeant, E. P., Dempsey, B., Eds.; IUPAC Chemical Data Series, No. 23; Pergamon Press: Oxford, UK, 1979.
    • (1979) Ionisation Constants of Organic Acids in Aqueous Solution
  • 29
    • 0242429868 scopus 로고    scopus 로고
    • Note
    • -1). An intermolecular H-bond is not formed in diethyl ether nor in di-n-butyl ether (ref 23a).
  • 30
    • 0242429869 scopus 로고    scopus 로고
    • Note
    • 4 (up to 70% acetonitrile, THF, DMSO, and pyridine). See Experimental Section and Supporting Information for details.
  • 33
    • 0002429883 scopus 로고
    • Patai S., Ed.; Wiley, New York, Chapter 5
    • Richardson, W. H. In The chemistry ofperoxides; Patai S., Ed.; Wiley: New York, 1983; Chapter 5, pp 129-160.
    • (1983) The Chemistry Ofperoxides , pp. 129-160
    • Richardson, W.H.1
  • 34
    • 0242513274 scopus 로고    scopus 로고
    • Note
    • ./ROH are 15.1 (MeOH), 15.9 (EtOH), 16.1 (n-propanol, n-butanol), 17.1 (2-propanol), and 19.2 (tert-butyl alcohol, tert-pentanol), see ref 22.
  • 36
    • 0242681829 scopus 로고    scopus 로고
    • note
    • . can therefore be neglected.
  • 38
    • 0242598004 scopus 로고    scopus 로고
    • Note
    • Electron transfer from un-ionized phenols to electrophilic radicals is occasionally proposed to be the rate-controlling step (followed by rapid proton loss) as an alternative to direct H-atom abstraction.
  • 39
    • 0242429865 scopus 로고    scopus 로고
    • Note
    • A large fraction of the papers identified in ref 3 involved studies on dpph• + antioxidant reactions in alcoholic solvents (generally methanol or ethanol).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.