期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 20, 页码 9451-9454出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo501531a
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资金
- US National Institute of Health [2R01GM50422]
The preparation and full characterization of the 4-(nitrophenyl)phenoxyl radical, 2,6-diibutyl-4-(4'-nitrophenyl) phenoxyl radical (Bu2NPArO center dot) is described. This is a rare example of an isolable and crystallographically III characterized phenoxyl radical and is the only example in which the parent phenol is also crystallographically well-defined. Analysis of EPR spectra indicates some spin delocalization onto the secondary aromatic ring and nitro group. Equilibrium studies show that the corresponding phenol has an 0 H bond dissociation free energy (BDFE) of 77.8 +/- 0.5 kcal mo1-1 in MeCN (77.5 +/- 0.5 kcal mol(-1) in toluene). This value is higher than related isolated phenoxyl radicals, making this a useful reagent for hydrogen atom transfer (HAT) studies. Additional thermochemical and spectroscopic parameters are also discussed.
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