DOI: 10.1246/bcsj.40.1058. Studies of the Electrolytic Reduction Mechanism of Anthracene, Benzophenone and Anthraquinone by the Use of Polarography and Electron Spin Resonance Spectroscopy

Studies of the Electrolytic Reduction Mechanism of Anthracene, Benzophenone and Anthraquinone by the Use of Polarography and Electron Spin Resonance Spectroscopy

10.1246/bcsj.40.1058

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The electrochemical reduction mechanism of anthracene, benzophenone and anthraquinone was studied in N,N′-dimethylformamide (DMF) and/or its water mixture by means of polarography and electron spin resonance spectroscopy (ESR). The polarograms of these compounds consisted of two well-defined waves in anhydrous DMF: the first wave corresponds to the formation of the anion radical and the second wave to the reduction of the anion radical to the dinegative anion. When water was added, the limiting current of the first wave increased at the expense of the second wave. In order to elucidate the reduction mechanism of these molecules in DMF-water mixture, the kinetic behavior of the anion radical was studied by the ESR method. It has been found that the reduction of anthracene is understood by the protonation mechanism, but that of anthraquinone is not explained by the protonation mechanism at all; the disproportionation of the anion radical must be considered. For the reduction of benzophenone both the protonation and the disproportionation mechanism must be taken into consideration.

Bibliography

Umemoto, K. (1967). Studies of the Electrolytic Reduction Mechanism of Anthracene, Benzophenone and Anthraquinone by the Use of Polarography and Electron Spin Resonance Spectroscopy. Bulletin of the Chemical Society of Japan, 40(5), 1058â1065.

Authors 1

Kisaburo Umemoto (first)

References 21 Referenced 44

{'key': '2024011821043180900_r1'}
{'key': '2024011821043180900_r2'}
10.1149/1.2430379
{'key': '2024011821043180900_r4'}
{'key': '2024011821043180900_r5'}
10.1149/1.2427738
10.1246/bcsj.36.1539
10.1246/bcsj.37.822
10.1038/1821784a0
10.1039/qr9621600163
10.1135/cccc19530311
10.1135/cccc19530597
10.1021/ac60236a005
10.1063/1.1742021
10.1063/1.1701296
10.1063/1.1733110
{'key': '2024011821043180900_r17'}
{'key': '2024011821043180900_r18'}
10.1021/ja01075a011
10.1016/0013-4686(64)80014-1
10.1135/cccc19654033

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 9:06 p.m.)
Deposited	1 year, 7 months ago (Jan. 18, 2024, 4:05 p.m.)
Indexed	1 year, 3 months ago (June 3, 2024, 7:19 p.m.)
Issued	58 years, 4 months ago (May 1, 1967)
Published	58 years, 4 months ago (May 1, 1967)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	58 years, 4 months ago (May 1, 1967)

Funders 0

None

BibTeX

@article{Umemoto_1967, title={Studies of the Electrolytic Reduction Mechanism of Anthracene, Benzophenone and Anthraquinone by the Use of Polarography and Electron Spin Resonance Spectroscopy}, volume={40}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.40.1058}, DOI={10.1246/bcsj.40.1058}, number={5}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Umemoto, Kisaburo}, year={1967}, month=may, pages={1058–1065} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        6,
        3
      ]
    ],
    "date-time": "2024-06-03T23:19:31Z",
    "timestamp": 1717456771295
  },
  "reference-count": 21,
  "publisher": "Oxford University Press (OUP)",
  "issue": "5",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            1967,
            5,
            1
          ]
        ],
        "date-time": "1967-05-01T00:00:00Z",
        "timestamp": -84326400000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "https://academic.oup.com/pages/standard-publication-reuse-rights"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1967,
        5,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title>\n               <jats:p>The electrochemical reduction mechanism of anthracene, benzophenone and anthraquinone was studied in N,N\u2032-dimethylformamide (DMF) and/or its water mixture by means of polarography and electron spin resonance spectroscopy (ESR). The polarograms of these compounds consisted of two well-defined waves in anhydrous DMF: the first wave corresponds to the formation of the anion radical and the second wave to the reduction of the anion radical to the dinegative anion. When water was added, the limiting current of the first wave increased at the expense of the second wave. In order to elucidate the reduction mechanism of these molecules in DMF-water mixture, the kinetic behavior of the anion radical was studied by the ESR method. It has been found that the reduction of anthracene is understood by the protonation mechanism, but that of anthraquinone is not explained by the protonation mechanism at all; the disproportionation of the anion radical must be considered. For the reduction of benzophenone both the protonation and the disproportionation mechanism must be taken into consideration.</jats:p>",
  "DOI": "10.1246/bcsj.40.1058",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        7,
        20
      ]
    ],
    "date-time": "2006-07-20T01:06:22Z",
    "timestamp": 1153357582000
  },
  "page": "1058-1065",
  "source": "Crossref",
  "is-referenced-by-count": 44,
  "title": "Studies of the Electrolytic Reduction Mechanism of Anthracene, Benzophenone and Anthraquinone by the Use of Polarography and Electron Spin Resonance Spectroscopy",
  "prefix": "10.1093",
  "volume": "40",
  "author": [
    {
      "given": "Kisaburo",
      "family": "Umemoto",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Chemistry Institute, Faculty of Science, Kyoto University"
        }
      ]
    }
  ],
  "member": "286",
  "published-online": {
    "date-parts": [
      [
        2006,
        3,
        27
      ]
    ]
  },
  "reference": [
    {
      "key": "2024011821043180900_r1"
    },
    {
      "key": "2024011821043180900_r2"
    },
    {
      "key": "2024011821043180900_r3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1149/1.2430379"
    },
    {
      "key": "2024011821043180900_r4"
    },
    {
      "key": "2024011821043180900_r5"
    },
    {
      "key": "2024011821043180900_r6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1149/1.2427738"
    },
    {
      "key": "2024011821043180900_r7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.36.1539"
    },
    {
      "key": "2024011821043180900_r8",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.37.822"
    },
    {
      "key": "2024011821043180900_r9",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/1821784a0"
    },
    {
      "key": "2024011821043180900_r10",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/qr9621600163"
    },
    {
      "key": "2024011821043180900_r11",
      "doi-asserted-by": "publisher",
      "DOI": "10.1135/cccc19530311"
    },
    {
      "key": "2024011821043180900_r12",
      "doi-asserted-by": "publisher",
      "DOI": "10.1135/cccc19530597"
    },
    {
      "key": "2024011821043180900_r13",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ac60236a005"
    },
    {
      "key": "2024011821043180900_r14",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1742021"
    },
    {
      "key": "2024011821043180900_r15",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1701296"
    },
    {
      "key": "2024011821043180900_r16",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1733110"
    },
    {
      "key": "2024011821043180900_r17"
    },
    {
      "key": "2024011821043180900_r18"
    },
    {
      "key": "2024011821043180900_r19",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01075a011"
    },
    {
      "key": "2024011821043180900_r20",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0013-4686(64)80014-1"
    },
    {
      "key": "2024011821043180900_r21",
      "doi-asserted-by": "publisher",
      "DOI": "10.1135/cccc19654033"
    }
  ],
  "container-title": "Bulletin of the Chemical Society of Japan",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/40/5/1058/55884603/bcsj.40.1058.pdf",
      "content-type": "application/pdf",
      "content-version": "vor",
      "intended-application": "syndication"
    },
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/40/5/1058/55884603/bcsj.40.1058.pdf",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        18
      ]
    ],
    "date-time": "2024-01-18T21:05:51Z",
    "timestamp": 1705611951000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://academic.oup.com/bcsj/article/40/5/1058/7371254"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1967,
        5,
        1
      ]
    ]
  },
  "references-count": 21,
  "journal-issue": {
    "issue": "5",
    "published-online": {
      "date-parts": [
        [
          2006,
          3,
          27
        ]
      ]
    },
    "published-print": {
      "date-parts": [
        [
          1967,
          5,
          1
        ]
      ]
    }
  },
  "URL": "http://dx.doi.org/10.1246/bcsj.40.1058",
  "relation": {},
  "ISSN": [
    "0009-2673",
    "1348-0634"
  ],
  "subject": [],
  "published-other": {
    "date-parts": [
      [
        1967,
        5
      ]
    ]
  },
  "published": {
    "date-parts": [
      [
        1967,
        5,
        1
      ]
    ]
  }
}