1992
DOI: 10.1139/v92-021
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Substituent and charge distribution effects on the redox potentials of radicals. Thermodynamics for homolytic versus heterolytic cleavage in the 1-naphthylmethyl system

Abstract: Can. J. Chem. 70, 121 (1992). The electrochemical oxidation and reduction potentials of a number of substituted 1-methylnaphthalenes (la-1) and 1-naphthylmethyl radicals (2a-1') as well as 2-methylnaphthalene (3) and the 2-naphthylmethyl radical (4') have been measured by cyclic voltammetry and photomodulation voltammetry. The oxidation potentials correlate with a+ (p+ = -7.1 and -8.4 for 1 and 2' respectively) while the reduction potentials correlate with a (p-= 10.1 and 13.0 for 1 and 2' respectively). The r… Show more

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Cited by 22 publications
(11 citation statements)
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“…Variation in substituents (X) on the naphthalene ring varies the oxidation potential of the 1-naphthylmethyl radical and, thus, the rate of electron transfer. These oxidation potentials were shown to correlate with a+ (p+ = -8.4) (15). The rates of electron transfer agreed very well with Marcus theory in both the normal and inverted regions (1 1, 12).…”
Section: (7)supporting
confidence: 63%
“…Variation in substituents (X) on the naphthalene ring varies the oxidation potential of the 1-naphthylmethyl radical and, thus, the rate of electron transfer. These oxidation potentials were shown to correlate with a+ (p+ = -8.4) (15). The rates of electron transfer agreed very well with Marcus theory in both the normal and inverted regions (1 1, 12).…”
Section: (7)supporting
confidence: 63%
“… a The reduction potentials of 1 , 2 , and 3 , E X | X •– (1/2) / V vs SCE, measured for acetonitrile (Figure ), are listed in the parentheses. For naphthalene and 1-methylnaphthalene, E X | X •– (1/2) ≈ −2.5 V vs SCE; , for dansylamide, E X | X •– (1/2) ≈ −2.05 V vs SCE; and for prodan, E X | X •– (1/2) ≈ −2.09 V vs SCE …”
mentioning
confidence: 99%
“…The essence of the PVA method consists of that the intensity of light and, correspondingly, the concentration of intermediates that are generated uniformly throughout the solution bulk (the near-electrode layer) is modulated with the aid of a chopper in a certain range of frequencies (in works [15][16][17][18][22][23][24][25][26][27], this is 20-250 Hz) and the dependence of the current of intermediates approaching the electrode by means of diffusion on the electrode potential (photovoltammogram) is measured at the same frequency. In view of the bulk character of the generation of intermediates, the PVA method is applicable only for the determination of E 0 for relatively long-lived radicals and requires, correspondingly, a high degree of purification of a nonaqueous solvent (acetonitrile).…”
Section: Combined Methods: Combination Of the Nonelectrochemical (Or mentioning
confidence: 99%