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

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1013-1016
Number of pages4
JournalTetrahedron
Volume69
Issue number3
DOIs
Publication statusPublished - 2013 Jan 21

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Keywords

  • Amides
  • Anilides
  • Hydrogen bonding
  • Isomerization
  • Rotamers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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