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

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

doi:10.1016/j.tet.2012.11.096

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

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

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1013-1016
Number of pages	4
Journal	Tetrahedron
Volume	69
Issue number	3
DOIs	https://doi.org/10.1016/j.tet.2012.11.096
Publication status	Published - 2013 Jan 21

Keywords

Amides
Anilides
Hydrogen bonding
Isomerization
Rotamers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.11.096

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title = "Rotational isomerism in 2,4,6-tri-tert-butylanilides",

abstract = "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.",

keywords = "Amides, Anilides, Hydrogen bonding, Isomerization, Rotamers",

author = "Nobutaka Ototake and Isao Takahashi and Shiori Tsukagoshi and Tatsuki Maeda and Osamu Kitagawa",

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AU - Ototake, Nobutaka

AU - Takahashi, Isao

AU - Tsukagoshi, Shiori

AU - Maeda, Tatsuki

AU - Kitagawa, Osamu

PY - 2013/1/21

Y1 - 2013/1/21

N2 - 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.

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.

KW - Amides

KW - Anilides

KW - Hydrogen bonding

KW - Isomerization

KW - Rotamers

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JO - Tetrahedron

JF - Tetrahedron

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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