Synthesis of Optically Active Polyamides Having Axially Dissymmetric 1,1'-Binaphthalene-2,2'-dicarboxylic Acid Component and Their Optical Resolution Ability as Chiral Adsorbent for HPLC.

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概要

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• Optically active polyamides <B>4a</B>–<B>4c</B> were synthesized from the polycondensation of axially dissymmetric 1,1′-binaphthalene-2,2′-dicarbonyl dichloride (<B>2</B>) with 1,4-benzenediamine, 1,6-hexanediamine, and 1,10-decanediamine, respectively. CD spectra of the polyamides <B>4a</B>–<B>4c</B> are essentially the same as those of the corresponding model diamides <B>6a</B>–<B>6c</B> prepared from <B>2</B> and benzenamine, 1-hexanamine, and 1-decanamine, respectively. This similarity indicates that the conformation of the 1,1′-binaphthalene-2,2′-dicarboxamide moieties of the polyamides <B>4a</B>–<B>4c</B> in solution state are rather similar to those of the corresponding model diamides <B>6a</B>–<B>6c</B>. Several axially chiral biaryl compounds and 3,5-dinitrophenylcarbamates (3,5-DNPCs) derived from 1-aryl-1-alkanols were resolved by HPLC equipped with the columns packed the chiral stationary phases (CSPs) prepared from <B>4a</B>–<B>4c</B> adsorbed on spherical silica gel. A main control factor for the chiral discrimination seems to be the hydrogen bonding between the amide groups of the CSPs and the hydrogen-bonding sites of the atropisomeric biaryls. The donor–acceptor interaction between the binaphthalene moiety of the CSPs and the 3,5-dinitrobenzene moiety of the 3,5-DNPCs may also be important for the chiral discrimination of the 3,5-DNPCs.

• 公益社団法人 日本化学会の論文

著者

• Tamai Yasufumi

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Oi Shuichi

  Department Of Applied Chemistry Graduate School Of Engineering Tohoku University

• Matsuzaka Yutaka

  Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University

• Miyano Sotaro

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

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