A pseudo-rotaxane of α-cyclodextrin and a two-station axis molecule consisting of pyridinium and decamethylene moieties, and its deuteration in deuterium oxide. Issue 33 (17th August 2017)

• Record Type: Journal Article
• Authors: Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira
• Is Part Of: Tetrahedron. Volume 73:Issue 33(2017)
• Page Start: 4988
• Page End: 4993
• Publication Date: 2017-08-17
• Subjects: Pseudo-rotaxane -- α-Cyclodextrin -- Two-station axis molecule -- Methylated pyridinium moieties -- Deuteration; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.05.044
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We prepared a two-station axis molecule possessing a 2-methylpyridinium moiety at an end, which regulates the direction of inclusion by α-cyclodextrin (α-CD). In the two-station axis molecule, the two decamethylene station moieties are linked through a pyridinium, over which α-CD can shuttle rather freely between the stations. We observed the formation of pseudo-rotaxane from the two-station axis molecule and α-CD at higher temperatures (≥50 °C). During the formation of pseudo-rotaxane in D2 O, we happened to find that the methyl and methylene groups on the 2- and 4-positions of pyridinium moieties underwent α-CD-catalyzed deuteration. The deuteration proceeded faster at a higher temperature. The apparent activation energy was estimated from the Arrhenius plot. Graphical abstract: