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Volumn 122, Issue 10, 2000, Pages 2355-2360

Hydrogen atom abstraction kinetics from intramolecularly hydrogen bonded ubiquinol-0 and other (poly)methoxy phenols

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; HYDROGEN; PHENOL DERIVATIVE; UBIQUINOL CYTOCHROME C REDUCTASE;

EID: 0034654215     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9937674     Document Type: Article
Times cited : (171)

References (44)
  • 7
    • 0343157000 scopus 로고    scopus 로고
    • note
    • 4
  • 9
    • 0343592490 scopus 로고    scopus 로고
    • note
    • 4 is recalculated by using the equilibrium constants, the concentration of the pure solvent, and eq 5.
  • 11
    • 0343592488 scopus 로고    scopus 로고
    • note
    • 12
  • 13
    • 0343156999 scopus 로고    scopus 로고
    • note
    • 2-PhOH equals 1:31:2.6.
  • 15
    • 0342287444 scopus 로고    scopus 로고
    • note
    • b is caused by the effect of the position of methyl substituent.
  • 16
    • 0343156998 scopus 로고    scopus 로고
    • note
    • 17 computed transition states for hydrogen atom abstraction from several para-substituted phenols by hydroperoxyl and methylperoxyl radicals at the HF/STO-3G level, finding O-H-O angles of 180̊, in contrast to our results for o- and p-methoxyphenol.
  • 18
    • 0342722548 scopus 로고    scopus 로고
    • note
    • The DFT calculations on 2-methoxyphenol show that on formation of the intramolecular hydrogen bond the positive (Mulliken) charge on this hydrogen increases slightly, from 0.315 to 0.331, consequently the rate for reaction with the electrophilic alkoxyl radical may decrease.
  • 19
    • 0342287442 scopus 로고    scopus 로고
    • note
    • + values from ref 21.
  • 22
    • 0342722545 scopus 로고    scopus 로고
    • note
    • -1.
  • 24
    • 0343156992 scopus 로고    scopus 로고
    • note
    • + values from ref 21.
  • 29
    • 0343156991 scopus 로고    scopus 로고
    • note
    • The observed rate constant for 2,6-dimethoxyphenol in tert-butyl alcohol is higher than could be expected from the hydrogen bond accepting properties of the solvent. This may be caused by steric hindrance to the formation of the intermolecular hydrogen bond.
  • 30
    • 0343156989 scopus 로고    scopus 로고
    • Data from refs 3 and 4
    • Data from refs 3 and 4.
  • 31
    • 0029680920 scopus 로고    scopus 로고
    • Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 8, 6790-1. Correction: Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 12485.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8
    • Banks, J.T.1    Ingold, K.U.2    Lusztyk, J.3
  • 32
    • 0030475398 scopus 로고    scopus 로고
    • Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 8, 6790-1. Correction: Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1996, 118, 12485.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12485
    • Banks, J.T.1    Ingold, K.U.2    Lusztyk, J.3
  • 33
    • 0343156988 scopus 로고    scopus 로고
    • note
    • -1 from the kinetic results.
  • 35
    • 0343156984 scopus 로고    scopus 로고
    • note
    • 1 for the experimental intermolecular hydrogen bond enthalpies of 2-methoxyphenol and 4-methoxyphenol with ethyl acetate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.