Electronic Structures and Oxidation Potentials of Some Azulene Derivatives.

• Kurihara Teruo

  Department of Chemistry, Faculty of Science, Josai University

• Suzuki Takanori

  Department of Chemistry, Faculty of Science, Hokkaido University

• Wakabayashi Hidetsugu

  Department of Chemistry, Faculty of Science, Josai University

• Ishikawa Sumio

  Department of Chemistry, Faculty of Science, Josai University

• Shindo Kimio

  Department of Chemistry, Faculty of Science, Josai University

• Shimada Yuji

  Department of Chemistry, Faculty of Science, Tohoku University

• Chiba Hiroshi

  Department of Chemistry, Faculty of Science, Tohoku University

• Miyashi Tsutomu

  Department of Chemistry, Faculty of Science, Tohoku University

• Yasunami Masafumi

  Department of Industrial Chemistry, Nihon University

• Nozoe Tetsuo

  Tokyo Research Lboratories, Kao Corporation

書誌事項

タイトル別名

• Electronic Structures and Oxidation Pot

抄録

The electronic structures of azulene (1) and its alkylated derivatives were investigated on the basis of MO calculations by MNDO and PM3 method. There results were experimentally evaluated by measuring the oxidation potentials (E^ox) of 1 and its alkylated derivatives, from which the additive property on E^ox was suggested as shown by E^ox(Az.subst) = E^ox(AZ) − 0.10n_1,3 + 0.06n₂ − 0.02n_4,8 − 0.11n_5,7 − 0.01n₆. Thus, the alkyl groups at the 1,3- and 5,7-positions lower the E^ox values by ca. 0.1 V, and stronger donating properties were observed for 3-methylguaiazulene (E^ox = +0.53 V) and 3,3′-biguaiazulene (E^ox = +0.40 V). The redox properties of guaiazulenyl sulfides which were prepared from guaiazulene via a phenylsulfonylthio derivative were also studied. Unlike the alkylated azulenes they underwent reversible one-electron oxidations and exhibited stronger donating properties (E^ox = +0.40 – +0.44).

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 69 (7), 2003-2008, 1996

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390282679098851584
• NII論文ID: 130004149610
• NII論文ID: 10008906018
• NII書誌ID: AA00580132
• DOI: 10.1246/bcsj.69.2003
• ISSN: 13480634
• ISSN: 00092673
• NDL書誌ID: 4060465
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4060465
• Web Site: https://academic.oup.com/bcsj/article-pdf/69/7/2003/56191696/bcsj.69.2003.pdf
• 本文言語コード: en
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