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Volumn 74, Issue 15, 2009, Pages 5163-5173

Accurate oxidation potentials of benzene and biphenyl derivatives via electron-transfer equilibria and transient kinetics

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SUBSTITUTION; ALKYL-SUBSTITUTED DERIVATIVES; BENZENE AND TOLUENE; BIPHENYL DERIVATIVES; ELECTRON TRANSFER KINETICS; ELECTRON-TRANSFER; EQUILIBRIUM MEASUREMENTS; ETHYL ACETATES; HEXAMETHYLBENZENE; METHYLENE CHLORIDE; NANOSECOND TRANSIENT ABSORPTION; OXIDATION POTENTIALS; RADICAL CATIONS; SOLVENT STABILIZATION; TRANSIENT KINETICS; TRIFLUOROACETIC ACIDS;

EID: 68049102204     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9011267     Document Type: Article
Times cited : (141)

References (75)
  • 36
    • 68049088269 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Steenken, S. Landolt-Börnstein 1985, 13e, 147.
    • (1985) Landolt-Börnstein , vol.13 e , pp. 147
    • Steenken, S.1
  • 44
    • 36349025758 scopus 로고    scopus 로고
    • For an analogous approach used for equilibration between two excited triplet states, see
    • For an analogous approach used for equilibration between two excited triplet states, see: Merkel, P. B.; Dinnocenzo, J. P. J. Photochem. and Photobiol. A, Chem. 2008, 193, 110.
    • (2008) J. Photochem. and Photobiol. A, Chem , vol.193 , pp. 110
    • Merkel, P.B.1    Dinnocenzo, J.P.2
  • 47
    • 68049089348 scopus 로고    scopus 로고
    • As defined in the text, the ratio of the optical densities (OD ∞/OD0) is equal to ratio of the extinction coefficients (εBP•+/εB•, at the analyzing wavelength. Thus, from this ratio and the experimentally determined OD0 the nominator in eq 7, OD∞, OD0, can be calculated. Alternatively, and more accurately, OD∞/OD 0) is obtained from the reciprocal of the intercept of a plot of 1/(OD, OD0) vs [B, BP, Cf. ref 14
    • 0) vs [B]/[BP]. Cf. ref 14.
  • 61
    • 68049086211 scopus 로고    scopus 로고
    • Lias, S. G. Ionization Energy Evaluation. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, http://webbook.nist.gov. See the Supporting Information for ionization potential values.
    • Lias, S. G. Ionization Energy Evaluation. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, http://webbook.nist.gov. See the Supporting Information for ionization potential values.
  • 65
    • 0001466425 scopus 로고    scopus 로고
    • The equilibrium constants between the radical cations of naphthalene and durene as well as between naphthalene and 1,2,3,5-tetramethylbenzene in acetonitrile were determined previously to be 2.4 and 0.24, respectively ( Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290). Based on the oxidation potential of durene (1.75 V vs SCE) and 1,2,3,5-tetramethylbenzene (1.82 V) an oxidation potential of 1.78 ± 0.01 V is calculated for naphthalene.
    • The equilibrium constants between the radical cations of naphthalene and durene as well as between naphthalene and 1,2,3,5-tetramethylbenzene in acetonitrile were determined previously to be 2.4 and 0.24, respectively ( Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290). Based on the oxidation potential of durene (1.75 V vs SCE) and 1,2,3,5-tetramethylbenzene (1.82 V) an oxidation potential of 1.78 ± 0.01 V is calculated for naphthalene.
  • 73
    • 0000828979 scopus 로고
    • β values: ethyl acetate=0.45; acetonitrile=0.31; methylene chloride=0.0; trifluoroacetic acid ∼ 0.0
    • Kamlet, M. J.; Abboud, J-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2887 (β values: ethyl acetate=0.45; acetonitrile=0.31; methylene chloride=0.0; trifluoroacetic acid ∼ 0.0).
    • (1983) J. Org. Chem , vol.48 , pp. 2887
    • Kamlet, M.J.1    Abboud, J.-L.M.2    Abraham, M.H.3    Taft, R.W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.