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10044226834
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note
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4.
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20
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10044233554
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note
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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.
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21
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37049127504
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Simonyi, M.; Fitos, I.; Kardos, J.; Lukovits, I. J. Chem. Soc., Chem. Commun. 1975, 252. Melander, L.; Saunders, W. H. In Reaction Rates of Isotopic Molecules; John Wiley and Sons: New York, 1980.
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Fitos, I.2
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22
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0004152918
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John Wiley and Sons: New York
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Reaction Rates of Isotopic Molecules
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Melander, L.1
Saunders, W.H.2
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23
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10044263939
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note
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-1.20
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24
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0037067554
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Brigati, G.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F. J. Org. Chem. 2002, 67, 4828-4832.
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25
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10044263940
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note
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3CN.23
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26
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0032311873
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Gorgy, K.; Lepretre, J.-C.; Saint-Aman, E.; Einhorn, C.; Einhorn, J.; Marcadal C.; Pierre, J.-L. Electrochim. Acta 1998, 44, 385-393.
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0037130656
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3042780720
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Mayer, J.M.1
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30
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10044249555
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note
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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.
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-
-
-
31
-
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10044286736
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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
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32
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0000664021
-
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Determined at 130 °C: Kim, S. S.; Lim, S. Y.; Ryou, S. S.; Lee, C. S.; Yoo, K. H. J. Org. Chem. 1993, 58, 192-196.
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Yoo, K.H.5
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33
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10044243266
-
-
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.
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-
-
-
34
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34247108511
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Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 699-711.
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-
39
-
-
10044229170
-
-
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.
-
-
-
-
40
-
-
0002904054
-
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Sarkanen, K. V., Ludwig, C. H., Eds., Wiley-Interscience: New York
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Sarkanen, K. V. Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig, C. H., Eds., Wiley-Interscience: New York, 1971; pp 95-195.
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Sarkanen, K.V.1
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41
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0036447091
-
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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.
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D'Acunzo, F.1
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Gentili, P.5
-
42
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0041629627
-
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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.
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Baiocco, P.1
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Gentili, P.5
-
44
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10044283750
-
-
note
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3CN (-0.68)12,13 is less negative than the p of the reaction with phenols.
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