2017年4月
Helical Folding of Hydroxy-Substituted N-Hetero-ortho-phenylenes Directed by Intramolecular Hydrogen Bonds
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 号
- 16
- 開始ページ
- 2353
- 終了ページ
- 2358
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/ejoc.201700102
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
Derivatives of the ortho-phenylene hexamer containing pyridine moieties and hydroxy groups were prepared through Negishi cross-coupling reactions between bis(chloropyridyl)biphenyl and alkoxy-substituted arylzinc reagents. X-ray diffraction analysis revealed a closed helical folding directed by pi-pi stacking and hydrogen bonds. No broadening or coalescence of H-1 NMR peaks was observed between 213 and 313 K, which indicates the high stability of the helical folding in CDCl3 solution. DFT calculations on the rotation of a single bond in the obtained compound indicated that the intramolecular hydrogen bonds led to exceptional stabilization of the closed helical folding. Right and left helices were separated by chiral column chromatography.
- リンク情報
- ID情報
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- DOI : 10.1002/ejoc.201700102
- ISSN : 1434-193X
- eISSN : 1099-0690
- Web of Science ID : WOS:000400328700021