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Volumn 27, Issue 3, 1998, Pages 707-739

Energetics of the O-H bond in phenol and substituted phenols: A critical evaluation of literature data

Author keywords

Bond dissociation enthalpy; Energetics; Phenol; Phenolic compounds; Substituent effects; Substituted phenols; Thermochemistry

Indexed keywords

CHEMICAL BONDS; DISSOCIATION; ENTHALPY; THERMOCHEMISTRY;

EID: 0001161617     PISSN: 00472689     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.556020     Document Type: Article
Times cited : (169)

References (127)
  • 3
    • 85033883172 scopus 로고
    • Am. Chem. Soc. Symp. Ser. No. 500, Washington. DC
    • Lipid Oxidation in Food, edited by A. J. St. Angelo, Am. Chem. Soc. Symp. Ser. No. 500, Washington. DC, 1992.
    • (1992) Lipid Oxidation in Food
    • St. Angelo, A.J.1
  • 6
  • 7
    • 0040308853 scopus 로고
    • Feb./Mar.
    • (g) Biochemist Feb./Mar. (1995).
    • (1995) Biochemist
  • 8
    • 85033881021 scopus 로고
    • Thermodynamics Research Center Data Series Thermodynamics Research Center, College Station
    • J. B. Pedley, Thermodynamic Data and Structures of Organic Compounds, Thermodynamics Research Center Data Series (Thermodynamics Research Center, College Station, 1994) Vol. I.
    • (1994) Thermodynamic Data and Structures of Organic Compounds , vol.1
    • Pedley, J.B.1
  • 9
    • 0003464216 scopus 로고    scopus 로고
    • NIST Standard Reference Database 69-February Release
    • NIST Chemistry WebBook, edited by W. G. Mallard (http:// webbook.nist.gov/chemistry); NIST Standard Reference Database 69-February 1997 Release, (a) E. P. Hunter and S. G. Lias;
    • (1997) NIST Chemistry WebBook
    • Mallard, W.G.1
  • 10
    • 0141917879 scopus 로고    scopus 로고
    • NIST Chemistry WebBook, edited by W. G. Mallard (http:// webbook.nist.gov/chemistry); NIST Standard Reference Database 69-February 1997 Release, (a) E. P. Hunter and S. G. Lias;
    • NIST Chemistry WebBook
    • Hunter, E.P.1    Lias, S.G.2
  • 12
    • 0003820285 scopus 로고    scopus 로고
    • Energetics of organic radicals
    • edited by J. A. Martinho Simões, A. Greenberg, and J. F. Liebman, Blackie, London, Chap. 2
    • W. Tsang, in Energetics of Organic Radicals, edited by J. A. Martinho Simões, A. Greenberg, and J. F. Liebman, SEARCH Series, Vol. 4 (Blackie, London, 1996), Chap. 2.
    • (1996) SEARCH Series , vol.4
    • Tsang, W.1
  • 21
    • 0003974162 scopus 로고
    • (Version 2) NIST Standard Reference Database 25; National Institute of Standards and Technology. Gaithersburg, MD
    • S. E. Stein, NIST Structures and Properties (Version 2) (NIST Standard Reference Database 25; National Institute of Standards and Technology. Gaithersburg, MD, 1994).
    • (1994) Nist Structures and Properties
    • Stein, S.E.1
  • 39
    • 16244368148 scopus 로고
    • V. D. Parker, J. Am. Chem. Soc. 114, 7458 (1992); 115, 1201 (1993).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1201
  • 41
    • 85033887835 scopus 로고    scopus 로고
    • -1
    • -1.
  • 44
    • 85033896267 scopus 로고    scopus 로고
    • -1. The discrepancy is due to a different choice of the enthalpy of formation of trans-azobenzene
    • -1. The discrepancy is due to a different choice of the enthalpy of formation of trans-azobenzene.
  • 45
    • 85033891888 scopus 로고    scopus 로고
    • See, for example, the references indicated in Ref. 28
    • See, for example, the references indicated in Ref. 28.
  • 48
    • 85033879687 scopus 로고    scopus 로고
    • -1 higher than benzene
    • -1 higher than benzene.
  • 56
    • 85033888416 scopus 로고    scopus 로고
    • -1) has not been included in the correction, since it is considered to be included in the empirical constant of Eq. (21)
    • -1) has not been included in the correction, since it is considered to be included in the empirical constant of Eq. (21).
  • 59
    • 85033902850 scopus 로고    scopus 로고
    • See Ref. 39
    • (b) See Ref. 39.
  • 60
    • 85033902123 scopus 로고    scopus 로고
    • note
    • .,g) and a minus sign should appear before the Gibbs energy of transfer.
  • 62
    • 0001463709 scopus 로고
    • (b) Later work by another group. [C. P. Andrieux, P. Hapiot, J. Pinson, and J.-M. Savéant, ibid. 115, 7783 (1993)] has shown that the use of second-harmonic ac voltammetry does not avoid the irreversibility problem. This is only accomplished by experiments made in faster time scales.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7783
    • Andrieux, C.P.1    Hapiot, P.2    Pinson, J.3    Savéant, J.-M.4
  • 63
    • 33748238315 scopus 로고
    • See, for example, K. S. Peters, Angew. Chem. Int. Ed. Engl. 33, 294 (1994); S. E. Braslavsky and G. E. Heibel, Chem. Rev. 92, 1381 (1992); D. Griller and D. D. M. Wayner, Pure Appl. Chem. 61, 717 (1989).
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 294
    • Peters, K.S.1
  • 64
    • 2342526764 scopus 로고
    • See, for example, K. S. Peters, Angew. Chem. Int. Ed. Engl. 33, 294 (1994); S. E. Braslavsky and G. E. Heibel, Chem. Rev. 92, 1381 (1992); D. Griller and D. D. M. Wayner, Pure Appl. Chem. 61, 717 (1989).
    • (1992) Chem. Rev. , vol.92 , pp. 1381
    • Braslavsky, S.E.1    Heibel, G.E.2
  • 65
    • 0001214979 scopus 로고
    • See, for example, K. S. Peters, Angew. Chem. Int. Ed. Engl. 33, 294 (1994); S. E. Braslavsky and G. E. Heibel, Chem. Rev. 92, 1381 (1992); D. Griller and D. D. M. Wayner, Pure Appl. Chem. 61, 717 (1989).
    • (1989) Pure Appl. Chem. , vol.61 , pp. 717
    • Griller, D.1    Wayner, D.D.M.2
  • 69
    • 85033897228 scopus 로고    scopus 로고
    • -1, based on older auxiliary data. This was the value used by Wayner et al. (Ref. 28)
    • -1, based on older auxiliary data. This was the value used by Wayner et al. (Ref. 28).
  • 77
    • 85033887459 scopus 로고    scopus 로고
    • .,aq)
    • .,aq).
  • 79
    • 85033892911 scopus 로고    scopus 로고
    • note
    • sln(O-H), as described in Sec. 3 (see also Table 3), assuming that ΔH(ECW) for 12 and PhOH are identical.
  • 82
    • 85033896576 scopus 로고    scopus 로고
    • -1 lower than the solution values in Table 4
    • -1 lower than the solution values in Table 4.
  • 87
    • 85033902147 scopus 로고    scopus 로고
    • -1
    • -1.
  • 91
    • 85033892218 scopus 로고    scopus 로고
    • acidH data and O-H bond dissociation energies estimated from solution studies
    • acidH data and O-H bond dissociation energies estimated from solution studies.
  • 94
    • 85033876609 scopus 로고    scopus 로고
    • Calculated data for O-H bond dissociation enthalpies which were not subject to experimental determination were not included in Table 4
    • Calculated data for O-H bond dissociation enthalpies which were not subject to experimental determination were not included in Table 4.
  • 102
    • 85033883300 scopus 로고    scopus 로고
    • Parent contributions have also been named ground state effects and polar contributions
    • Parent contributions have also been named ground state effects and polar contributions.
  • 103
    • 0004263533 scopus 로고
    • Cambridge University Press, Cambridge
    • C. D. Johnson, The Hammett Equation (Cambridge University Press, Cambridge, 1980).
    • (1980) The Hammett Equation
    • Johnson, C.D.1
  • 106
    • 85033873022 scopus 로고    scopus 로고
    • + data sets were used in Refs. 52, 78, and 84
    • + data sets were used in Refs. 52, 78, and 84.
  • 108
    • 85033877035 scopus 로고    scopus 로고
    • In the case of large resonance effects, these may also be felt at the meta position, although they are expected to be small compared to the inductive effects
    • In the case of large resonance effects, these may also be felt at the meta position, although they are expected to be small compared to the inductive effects.
  • 113
    • 85033894225 scopus 로고    scopus 로고
    • The difference in ΔD(O-H), observed in Table 4, between the "away" and "toward" conformers of 3-methylphenol is not zero, as it should be expected. This must be due to the limitations of the calculation method
    • The difference in ΔD(O-H), observed in Table 4, between the "away" and "toward" conformers of 3-methylphenol is not zero, as it should be expected. This must be due to the limitations of the calculation method.
  • 114
    • 85033882430 scopus 로고    scopus 로고
    • p=0.42). The latter value was preferred. The Hammett parameters were quoted from Ref. 91
    • p=0.42). The latter value was preferred. The Hammett parameters were quoted from Ref. 91.
  • 115
    • 85033877903 scopus 로고    scopus 로고
    • o for 4-methoxytetramethylphenol
    • o for 4-methoxytetramethylphenol.
  • 116
    • 85033897683 scopus 로고    scopus 로고
    • p=-0.60
    • p=-0.60.
  • 117
    • 85033880556 scopus 로고    scopus 로고
    • 2 was excluded from the correlation
    • 2 was excluded from the correlation.
  • 118
    • 85033887361 scopus 로고    scopus 로고
    • As stated in Ref. 81, the parameter a should not even be constant for all substituents
    • As stated in Ref. 81, the parameter a should not even be constant for all substituents.
  • 119
    • 85033902078 scopus 로고    scopus 로고
    • With a=1 the correlation is also good (r=0.974)
    • With a=1 the correlation is also good (r=0.974).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.