Rotational isomerism of the amide units in rotaxanes based on a cyclic tetraamide and secondary ammonium ions

文献情報

出版日 2019-02-20

DOI 10.1039/C9QO00096H

インパクトファクター 5.281

著者

Yukari Okuma, Toshihiro Tsukamoto, Takayuki Inagaki, Shinobu Miyagawa, Masaki Kimura, Masaya Naito, Hikaru Takaya, Tsuneomi Kawasaki, Yuji Tokunaga

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要旨

In this study, we synthesized the macrocyclic tetraamide 1, possessing four tertiary amide units, as a host for mono- and bis-ammonium ions, forming corresponding [2]pseudorotaxanes stabilized through hydrogen bonding between the components. [2]Rotaxanes comprising 1 as the macrocycle and mono- and bis-ammonium ions as the axle components were synthesized through imine bond formation. The tetraamide 1 exists as a mixture of rotamers in solution; in the [2]rotaxanes, however, the conformation of this component was controlled through intramolecular hydrogen bonding between the axle and macrocyclic components. In a nonpolar solvent (CDCl3), only one conformational isomer existed for each [2]rotaxane. On the other hand, in a polar solvent (DMSO-d6), the [2]rotaxane possessing a mono-ammonium ion in the axle was partially isomerized; only a single rotational isomer existed for the [2]rotaxane featuring a bis-ammonium ion in the axle, because of a complete set of hydrogen bonds, in this polar solvent.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Rotational isomerism of the amide units in rotaxanes based on a cyclic tetraamide and secondary ammonium ions

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