Substituent effects on the stabilities of phenoxyl radicals and the acidities of phenoxyl radical cations
Autor: | Frederick G. Bordwell, J.-P. Cheng |
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Rok vydání: | 1991 |
Předmět: | |
Zdroj: | Journal of the American Chemical Society. 113:1736-1743 |
ISSN: | 1520-5126 0002-7863 |
Popis: | Oxidation potentials for 35 phenoxide ions and 3 naphthoxide ions have been combined with their pK HA values to estimated homolytic bond dissociation energies (BDEs) for the O-H bonds in phenols. Comparison with literature values shows that there is remarkably good agreement ΔBDE values determined by different methods. A good correlation of E ox (A − ) values for p-GC 6 H 4 O − phenoxide ions with σ + constants was observed over a range of greater than 40 kcal/mol. The acidities of 35 phenoxyl radical cations have been estimated from pK HA , E ox (A − ), and E ox (HA) values. A good correlation of E ox (HA) vs pK HA •+ was observed from m-GC 6 H 4 OH •+ radical cations, but the points for para donors were found to deviate from the line |
Databáze: | OpenAIRE |
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