The DOI matches its Crossref record; 10 of the 10 references it cites were found in a registry or an index.
Bond Dissociation Energies of O−H Bonds in Substituted Phenols from Equilibration Studies
Abstract
Bond dissociation energies (BDE) of several phenolic compounds have been determined by studying the equilibration of couples of phenols and of the corresponding phenoxyl radicals by means of EPR spectroscopy. Measurements were carried out in highly concentrated solutions submitted to continuous photolysis in the presence of di- tert -butyl peroxide. Since under this experimental condition the decay of the phenoxyl radicals was slower than the hydrogen transfer reaction from phenols to phenoxyls, equilibrium concentrations of the two radicals were actually measured. Due to the fact that the radical species are continuously generated in solution, phenols giving short-lived phenoxyl radicals could also be investigated by this method. All of the examined phenols are characterized by O−H bonds weaker than that of the parent compound, PhOH, and their BDE values can be calculated to a good approximation by an additive rule using fixed contributions for the various substituents. Only in the case of the sterically crowded 4-methoxytetramethylphenol ( 5b ), where the p- methoxy substituent is compelled to stay out of the plane of the aromatic ring, is the experimental BDE remarkably different from the calculated value.
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Citations
Cites
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Bond Dissociation Enthalpy of .alpha.-Tocopherol and Other Phenolic Antioxidants
Lucarini, M., Pedulli, G. F., & Cipollone, M. (1994) · The Journal of Organic Chemistry · doi:10.1021/jo00096a061 · Cited by 175
Self-citationThe Surprisingly High Reactivity of Phenoxyl Radicals
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Mahoney, L. R., Mendenhall, G. D., & Ingold, K. U. (1973) · Journal of the American Chemical Society · doi:10.1021/ja00807a018 · Cited by 160
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THE CHEMISTRY OF VITAMIN E. VI. THE ADDITION OF DIENES TO PHENOLS AND HYDROQUINONES1, *
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Cited by
Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis
Quideau, S., Deffieux, D., Douat‐Casassus, C., & Pouységu, L. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201000044 · Cited by 2,730
Proton-coupled electron transfer
Huynh, M. H. V., & Meyer, T. J. (2007) · Chemical Reviews · doi:10.1021/cr0500030 · Cited by 1,659
Ingold, K. U., & Pratt, D. A. (2014) · Chemical Reviews · doi:10.1021/cr500226n · Cited by 531
Yehye, W. A., Rahman, N. A., Ariffin, A., Abd Hamid, S. B., Alhadi, A. A., Kadir, F. A., & Yaeghoobi, M. (2015) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2015.06.026 · Cited by 489
Flash Vacuum Pyrolysis of Methoxy-Substituted Lignin Model Compounds
Britt, P. F., Buchanan, A. C., Cooney, M. J., & Martineau, D. R. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo991479k · Cited by 255
Metadata
- Authors
- Lucarini, M., Pedrielli, P., Pedulli, G. F., Cabiddu, S., & Fattuoni, C.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1996-01-01
- Volume
- 61
- Issue
- 26
- Pages
- 9259-9263
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1975382808
- Cited by
- 291
- References
- 10
- FWCI
- 1.79
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lucarini, M., Pedrielli, P., Pedulli, G. F., Cabiddu, S., & Fattuoni, C. (1996). Bond Dissociation Energies of O−H Bonds in Substituted Phenols from Equilibration Studies. The Journal of Organic Chemistry. https://doi.org/10.1021/jo961039i
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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