The Electrochemical Oxidation of Substituted Catechols
Open accessAbstract
The oxidation of substituted catechols was studied by cyclic voltammetry, chronoamperometry, rotating ring‐disk electrode, and coulometry. The results showed that the quinones that were formed from the oxidation of substituted catechols reacted with the basic forms of the starting material to yield the dimeric product. These products were generally unstable and rapidly polymerized or underwent some other irreversible reaction to form an electroinactive product. For 3,4‐dihydroxyacetophenone and propriophenone, the intermediate was stable long enough to be observed in cyclic voltammetry. The rate of the coupling reaction was found to correlate well with the Hammett ρ‐σ parameters and indicated that there was substantial negative charge in the transition state. Finally, an analysis of the coulometric n ‐values along with the values indicated that the initial coupling product was a diphenyl ether. Analysis of the coulometry products showed extensive polymerization.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Quinones led to an increase in potential and a fall in pH at longer times due to their hydrolysis.
“The quinones led to an increase in potential and a fall in pH at longer times due to their hydrolysis.25”
From The role of dihydroxybenzenes and oxygen on the corrosion of steel in black liquor (1996) · cites this paper as [25]
The Conclusions (page unavailable) say that substituted catechols form quinones and that a different measure—the coulometric n-value—increases at long electrolysis times, attributing that increase to polymeric products and catechol depletion. The Results and Conclusions do not report a longer-term rise in potential or fall in pH caused by quinone hydrolysis (searched for hydrolysis and the claimed potential–pH changes). (LLM, conf=0.72)
Experimental — accuracy not yet measured
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
No references could be resolved yet.
Research works printed but not linked: 33
- D. L. Maricle and W. G. Hodgson, Anal. Chem., 37, 1562 (1965).
- D. T. Sawyer and J. L, Roberts, Jr., J. Electroanal. Chem. Interfacial Electrochem., 12, 90 (1966).
- M. E. Peover and B. S. White, Electrochim. Acta, 11, 1061 (1966).
- E. L. Johnson, K. H. Pool, and R. E. Hamm, Anal. Chem., 38, 183 (1966).
- J. E. A. Toni, This Journal, 116, 212 (1969).
- D. T. Sawyer, M. J. Gibian, M. M. Morrison, and E. T. Seo, J. Am. Chem. Soc., 100, 627 (1978).
- E. Lee-Ruff, Chem. Soc. Rev., 6, 195 (1977).
- C. Chern and J. San Filippo, Jr., J. Org. Chem., 42, 178 (1977).
- P. E. Whitson, H. W. VandenBorn, and D. H. Evans, Anal. Chem., 45, 1298 (1973).
- R. S. Nicholson and I. Shain, ibid., 37, 178 (1965).
- R. Stewart, J. P. O'Donnell, D. J. Cram, and B. Rickborn, Tetrahedron, 18, 917 (1962).
- K. Bowden, Chem. Rev., 66, 119 (1966).
- H. J. James and R. F. Broman, J. Phys. Chem., 75, 4019 (1971).
- M. D. Hawley and S. W. Feldberg, ibid., 70, 3459 (1966).
- M. M. Morrison, J. L. Roberts, Jr., and D. T. Saw- yer, Inorg. Chem., 18, 1971 (1979). REFERENCES
- R. N. Adams, M. D. Hawley, and S. W. Feldberg, J. Chem. Phys., 71, 851 (1967).
- M. D. Hawley, S. V. Tatawawadi, S. Piekarski, and R. N. Adams, J. Am. Chem. Soc., 89, 447 (1967).
- A. W. Sternson, R. McCreery, B. Feinberg, and R. N. Adams, J. Electroanal. Chem. Interracial Electrochem., 46, 313 (1973).
- L. Papouchado, G. Petrie, and R. N. Adams, ibid., 38, 389 (1972).
- L. Papouchado, G. Petrie, J. H. Sharp, and R. N. Adams, J. Am. Chem. Soc., 90, 5620 (1968).
- T. E. Young, J. R. Griswold, and M. H. Hulbert, J. Org. Chem., 39, 1980 (1974).
- A. Brun and R. Rosset, J. Electroanal. Chem. In- terracial Electrochem., 49, 287 (1974).
- J. Doskocil, Coll. Czech. Chem. Commun., 15, 780 (1950).
- G. Sivaramiah and V. R. Krishman, Indian J. Chem., 4, 541 (1966).
- D. I. Stom and S. N. Suslov, Biofizika, 21, 40 (1976).
- H. Musso, in "Oxidative Coupling of Phenols," W. I. Taylor and A. R. Battersley, Editors, pp. 1-94, Marcel Dekker, Inc., New York (1967).
- W. G. C. Forsyth and V. C. Quesnel, Biochim. Biophys. Acta., 25, 155 (1957).
- C. R. Dawson and W. B. Tarpley, N.Y. Acad. Sci. Ann., 100, 937 (1963).
- P. J. Kinlen, D. H. Evans, and S. F. Nelsen, J. Electroanal. Chem. Interracial Electrochem., 97, 265 (1979).
- E. Ritchie, J. Proc. R. Soc. N.S. Wales, 78, 134 (1945).
- J. F. W. McOmie, M. L. Watts, and D. E. West, Tetrahedron, 24, 2289 (1968).
- S. W. Feldberg, in "Electroanalytical Chemistry," Vol. 3, A. J. Bard, Editor, pp. 199-296, Marcel Dekker, Inc., New York (1969).
- P. J. Antikainen and U. Witikainen, Acta Chem. Scand., 27, 2075 (1973).
Cited by
Sorted by citations
The role of dihydroxybenzenes and oxygen on the corrosion of steel in black liquor
Kannan, S., & Kelly, R. G. (1996) · Corrosion Science · doi:10.1016/0010-938x(96)00186-2 · Cited by 16 · see citing works
- Authors
- Ryan, M. D., Yueh, A., & Chen, W.
- Affiliations
- Marquette University (US)
- ORCID
- Ryan, Michael D.
- Venue
- Journal of The Electrochemical Society
- Publisher
- The Electrochemical Society
- Published
- 1980-07-01
- Volume
- 127
- Issue
- 7
- Pages
- 1489-1495
- ISSN
- 0013-4651 (ISSN-L)
- 1945-7111
- OpenAlex
- W1968490027
- Cited by
- 210
- References
- 0
- Citations by year
- 2026: 5 · 2025: 3 · 2024: 2 · 2023: 5 · 2022: 2 · 2021: 1 · 2020: 2 · 2019: 8 · 2018: 9 · 2017: 10 · 2016: 6 · 2015: 12 · 2014: 14 · 2013: 2 · 2012: 12
- FWCI
- 1.10
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Journal of The Electrochemical Society (publishedVersion)
- e-Publications@Marquette (Marquette University) (submittedVersion)
- Funders
- Marquette University
- University Research Committee, Emory University
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Physical Sciences › Chemistry › Electrochemistry › Electrochemical Analysis and Applications
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- electrochemical oxidation, dimerization, coupling reactions, Hammett substituent constants, coulometry, polymerization, 3,4-dihydroxyacetophenone, diphenyl ether
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
