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Volumn 69, Issue 25, 2004, Pages 8963-8966

Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond. A kinetic study

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DEUTERIUM; ORGANIC SOLVENTS; REACTION KINETICS; STEREOCHEMISTRY;

EID: 10044290846     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048656o     Document Type: Article
Times cited : (39)

References (46)
  • 2
    • 0000434277 scopus 로고    scopus 로고
    • Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934-3935. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 393-427
    • Ishii, Y.1    Sakaguchi, S.2    Iwahama, T.3
  • 19
    • 10044226834 scopus 로고    scopus 로고
    • note
    • 4.
  • 20
    • 10044233554 scopus 로고    scopus 로고
    • note
    • Second-order kinetics are observed since the rate of the initial hydrogen atom transfer from the phenol to the PINO is much slower than the rate of recombination of the phenoxyl radical with the PINO.10 The second-order rate constants reported in Table 1 are those experimentally determined and were not divided by 2.
  • 23
    • 10044263939 scopus 로고    scopus 로고
    • note
    • -1.20
  • 25
    • 10044263940 scopus 로고    scopus 로고
    • note
    • 3CN.23
  • 29
    • 3042780720 scopus 로고    scopus 로고
    • Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T J. Am. Chem. Soc. 2002, 124, 11142-11147. Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390.
    • (2004) Annu. Rev. Phys. Chem. , vol.55 , pp. 363-390
    • Mayer, J.M.1
  • 30
    • 10044249555 scopus 로고    scopus 로고
    • note
    • Calculations by Mayer and co-workers24 have shown that in the transition state of the phenoxyl/phenol exchange more positive charge is present in the phenol moiety with respect to the starting phenol.
  • 31
    • 10044286736 scopus 로고    scopus 로고
    • note
    • Figure 3 represents a limit structure of the transition state that serves only to visualize the consequence of the electron shift occurring when the proton is only partially transferred (PCET). Of course, it must be considered that the positive charge in the ring is partially neutralized by the negative charge developing on oxygen, and thus in the transition state there actually is only a partial positive charge in the phenyl ring, in line with calculations.25
  • 33
    • 10044243266 scopus 로고    scopus 로고
    • note
    • It was possible to examine only a few solvents, since in many cases there were problems related to the solubility of the PINO generating system or to a fast reaction of PINO with the solvent.
  • 39
    • 10044229170 scopus 로고    scopus 로고
    • note
    • Lignin is a tridimensional polymer built from phenolic and nonphenolic phenylpropane units linked together by different bonds.35 A large number of phenolic ArOH groups and benzylic ArCH(OH)R groups are present.
  • 41
    • 0036447091 scopus 로고    scopus 로고
    • 2 system, has been reported in the literature; see: D'Acunzo, F.; Baiocco, P.; Fabbrini, M.; Galli, C.; Gentili, P. New J. Chem. 2002, 26, 1791-1794. Baiocco, P.; Barreca, A. M.; Fabbrini, M.; Galli, C.; Gentili, P. Org. Biomol. Chem. 2003, 1, 191-197.
    • (2002) New J. Chem. , vol.26 , pp. 1791-1794
    • D'Acunzo, F.1    Baiocco, P.2    Fabbrini, M.3    Galli, C.4    Gentili, P.5
  • 42
    • 0041629627 scopus 로고    scopus 로고
    • 2 system, has been reported in the literature; see: D'Acunzo, F.; Baiocco, P.; Fabbrini, M.; Galli, C.; Gentili, P. New J. Chem. 2002, 26, 1791-1794. Baiocco, P.; Barreca, A. M.; Fabbrini, M.; Galli, C.; Gentili, P. Org. Biomol. Chem. 2003, 1, 191-197.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 191-197
    • Baiocco, P.1    Barreca, A.M.2    Fabbrini, M.3    Galli, C.4    Gentili, P.5
  • 44
    • 10044283750 scopus 로고    scopus 로고
    • note
    • 3CN (-0.68)12,13 is less negative than the p of the reaction with phenols.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.