Rotational isomerism in 2,4,6-tri-tert-butylanilides

Nobutaka Ototake, Isao Takahashi, Shiori Tsukagoshi, Tatsuki Maeda, Osamu Kitagawa

研究成果: Article

抄録

Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.

元の言語English
ページ(範囲)1013-1016
ページ数4
ジャーナルTetrahedron
69
発行部数3
DOI
出版物ステータスPublished - 2013 1 21

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Anilides
Isomerization
Hydrogen bonds
Heating
2,4,6-tri-tert-butylanilide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Ototake, N., Takahashi, I., Tsukagoshi, S., Maeda, T., & Kitagawa, O. (2013). Rotational isomerism in 2,4,6-tri-tert-butylanilides. Tetrahedron, 69(3), 1013-1016. https://doi.org/10.1016/j.tet.2012.11.096

Rotational isomerism in 2,4,6-tri-tert-butylanilides. / Ototake, Nobutaka; Takahashi, Isao; Tsukagoshi, Shiori; Maeda, Tatsuki; Kitagawa, Osamu.

:: Tetrahedron, 巻 69, 番号 3, 21.01.2013, p. 1013-1016.

研究成果: Article

Ototake, N, Takahashi, I, Tsukagoshi, S, Maeda, T & Kitagawa, O 2013, 'Rotational isomerism in 2,4,6-tri-tert-butylanilides', Tetrahedron, 巻. 69, 番号 3, pp. 1013-1016. https://doi.org/10.1016/j.tet.2012.11.096
Ototake N, Takahashi I, Tsukagoshi S, Maeda T, Kitagawa O. Rotational isomerism in 2,4,6-tri-tert-butylanilides. Tetrahedron. 2013 1 21;69(3):1013-1016. https://doi.org/10.1016/j.tet.2012.11.096
Ototake, Nobutaka ; Takahashi, Isao ; Tsukagoshi, Shiori ; Maeda, Tatsuki ; Kitagawa, Osamu. / Rotational isomerism in 2,4,6-tri-tert-butylanilides. :: Tetrahedron. 2013 ; 巻 69, 番号 3. pp. 1013-1016.
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AU - Takahashi, Isao

AU - Tsukagoshi, Shiori

AU - Maeda, Tatsuki

AU - Kitagawa, Osamu

PY - 2013/1/21

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AB - Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in the solid state produced complete isomerization to the Z-rotamer.

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KW - Anilides

KW - Hydrogen bonding

KW - Isomerization

KW - Rotamers

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