Inclusion of Amine Isomers with Open-Chain Hosts Having a Partial Structure of p-tert-Butylthiacalixarene

Ikuko Miyoshi, Hayato Sonehara, Jun Ogihara, Tomoaki Matsumoto, Naoya Morohashi, Tetsutaro Hattori

研究成果: Article査読

抄録

Porous materials, which can capture a specific compound from a hard-to-separate molecular mixture, are strongly desired for practical separation and purification processes. Aiming to develop such materials, we have investigated the performance of our original host compounds, [3,3′-thiobis(5-tert-butyl-2-hydroxybenzene)-1,1′-diyl]diacetic acid (2) and its monopropyl ester (3), in discriminating among regio- or stereoisomers of three groups of amines, 2-, 3-, and 4-methylpyridine, 2-, 6-, and 8-methylquinoline, and cis- and trans-4-cyclohexanamine. Diacid 2 selectively included 4-methylpyridine in hexane and 3-methylpyridine in toluene in competitive inclusion among the three regioisomers. Mechanistic studies revealed that the inclusions of 3- and 4-methylpyridine are favored under kinetic and thermodynamic control, respectively. Solvent-dependent switching in guest selectivity was also observed in competitive inclusion among the methylquinoline isomers with diacid 2, whereas trans-4-methylcyclohexanamine was selectively included over the cis-isomer by monoester 3, as well as diacid 2, regardless of the solvent employed. X-ray crystallographic analysis of the resulting inclusion crystals suggests that the wide guest scope of the host compounds originates from their flexible ability to form complexes with amines.

本文言語English
ページ(範囲)7046-7058
ページ数13
ジャーナルJournal of Organic Chemistry
86
10
DOI
出版ステータスPublished - 2021 5 21

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Inclusion of Amine Isomers with Open-Chain Hosts Having a Partial Structure of p-tert-Butylthiacalixarene」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル