Resolution of optical isomers by high-performance liquid chromatography, using coated and bonded chiral charge-transfer complexing agents as stationary phases
Resolution of optical isomers by high-performance liquid chromatography, using coated and bonded chiral charge-transfer complexing agents as stationary phases
复制标题
使用涂覆且键合的手性电荷转移络合剂作为固定相，通过高效液相色谱法拆分旋光异构体
DOI：
10.1016/s0021-9673(00)82245-1
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发表时间：
1976
影响因子：
4.1
通讯作者：
E. Gil
中科院分区：
文献类型：
--
作者：
F. Mikeš;G. Boshart;E. Gil
用高效液相色谱法拆分了10个外消旋螺烯（[5]~[14]）和2个双螺烯{二菲并[4，3-a; 3′，4 ′-o]芘（I）和8，20-二溴二菲并[4，3-a; 4′，3 ′-j]芘（II）}。以R（-）-和S（+）-2-（2，4，5，7-四硝基-9-芴亚氨基氧基）丙酸（TAPA）以及丁酸（TABA）、异戊酸（TAIVA）和己酸（TAHA）衍生的三种R（-）-同系物为手性电荷转移（C.T.）复合物形成固定相，在原位二氧化硅微粒。在C.T.的手性中心的基团的庞大性。受体对于CT的轻松解析至关重要捐助者。[6]-[14]-螺旋烯和双螺旋烯I和II在R（−）-TAPA上完全分离。另一方面，[5]-螺烯的光学异构体只能在R（−）-TABA上分离，基线拆分需要10个循环步骤。R（-）-TAPA也以键合固相和盐的形式掺入。给出了分辨率因子r，提出了一种分辨率机制，并讨论了该方法的适用范围及其意义。
Ten racemic helicenes ([5] to [14]) and two double helicenes {diphenanthro[4,3-a; 3′,4′-o]picene (I) and 8,20-dibromodiphenanthro[4,3-a; 4′,3′-j]chrysene (II)} were resolved using high-performance liquid chromatography. R(−)- and S(+)-2-(2,4,5,7-tetranito-9-fluorenylideneaminooxy)propionic acid (TAPA) and three R(−)-homologues derived from butyric (TABA), isovaleric (TAIVA) and hexanoic (TAHA) acids were used as chiral charge-transfer (C.T.) complex-forming stationary phases,in situcoated on silica microparticles. The bulkiness of the group at the chiral centre of the C.T. acceptor is critical for the ease of resolution of the C.T. donors. The [6]-[14]-helicenes and the double helicenes I and II were completely resolved on R(−)-TAPA. On the other hand, the optical isomers of [5]-helicene could be separated only on R(−)-TABA and baseline resolution required ten recycling steps. R(−)-TAPA was also incorporated as a bonded solid phase and as a salt. The resolution factors,r, are given, a mechanism of resolution is proposed and the scope of the method and its significance are discussed.