ID | JOS-j.tet.2009.11.076 |
著者:名前 | |
著者:別形式 | Mukano, Yoko / Momochi, Mai / Takanashi, Yuriko / Suzuki, Mitsuaki / Wakabayashi, Hidetsugu / Teramae, Hiroyuki / Kobayashi, Keiji |
著者:カナ | |
著者:所属 | 城西大学大学院理学研究科 / 城西大学大学院理学研究科 / 城西大学大学院理学研究科 / 城西大学大学院理学研究科 / 城西大学理学部 / 城西大学理学部 / 城西大学理学部 |
著者:所属(別形式) | Josai Universtiy, Graduate School of Material Scinece / Josai Universtiy, Graduate School of Material Scinece / Josai Universtiy, Graduate School of Material Scinece / Josai Universtiy, Graduate School of Material Scinece / Josai Universtiy, Department of Chemistry / Josai Universtiy, Department of Chemistry / Josai Universtiy, Department of Chemistry |
著者版フラグ | author |
出版者 | Elsevier |
NCID | AA00861787 |
冊子ISSN | 00404020 |
電子ISSN | 00404020 |
掲載誌名 | |
巻 | 66 |
号 | 3 |
刊行年月 | 2010-01 |
開始ページ | 605 |
終了ページ | 611 |
コンテンツ作成日 | 2009-10-29 |
コンテンツ修正日 | 2009-11-17 |
コンテンツ登録日 | 2009-11-20 |
識別番号:DOI | info:doi/10.1016/j.tet.2009.11.076 |
識別番号:DOI(リンク) | |
抄録 | The tautomeric structures and dynamic prototropic behavior of the products 1 and 2 obtained in the condensation reaction of 1,3-indandione and 2-pyridyl-1,3-indandione with p-toluidine, respectively, were investigated by 1H NMR spectroscopy and X-ray analysis. In the solid state, compound 1 is in an imino-enamine tautomeric form, whereas in solution it coexists with an imino-imino tautomeric form. Dynamic 1,5-prototropic interconversion of the imino-enamine form was revealed to be very fast at room temperature by temperature-dependent 1H NMR spectra. For 2, the imino-enamine form is the only species present in solution. The hydrogen of the enamine NH is hydrogen-bonded intramolecularly with the nitrogen in the pyridine ring. When the temperature is raised, the NH proton enters into dynamic 1,5-migration, which is accompanied by internal rotation around the pivot bond, which changes the hydrogen-bonding sites. For the condensation product 3 of 2-(2-quinolyl)-1,3-indandione with p-butylaniline, dynamic behavior similar to that found in 2 was observed also in 13C NMR spectra. |
キーワード | |
言語 | eng |
資源タイプ | text |
ジャンル | |
フォーマット | application/pdf |
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このアイテムを表示する:URI | |