Hydrogen Bonding, the Driving Force for Increased Host Selectivities in Two-Solvent Mixed Complexes of TETROL Comprising Both Favored (Aniline) and Disfavored Guests (o-Toluidine or Toluene),Crystal Growth & Design

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Hydrogen Bonding, the Driving Force for Increased Host Selectivities in Two-Solvent Mixed Complexes of TETROL Comprising Both Favored (Aniline) and Disfavored Guests (o-Toluidine or Toluene)
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2018-04-20 00:00:00 , DOI: 10.1021/acs.cgd.8b00364
Benita Barton ₁ , Sasha-Lee Dorfling ₁ , Eric C. Hosten ₁

Affiliation

In this work, we have shown that host–guest hydrogen bonding is intricately associated with host selectivity in supramolecular systems comprising host (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and guests aniline, toluene, and the toluidines. Competition experiments provided the host selectivity order, p-toluidine > aniline > m-toluidine > o-toluidine > toluene and, additionally, three crystalline two-guest mixed complexes containing aniline/o-toluidine, aniline/p-toluidine, and aniline/toluene; the overall host:guest ratio was 2:3. Crystal diffraction experiments showed the host packing to be consistently isostructural. Furthermore, only two of the three guests in the asymmetric unit are hydrogen bonded to the host; the third does not experience this interaction type even if possessing hydrogen-bonding capability (e.g., an amino functionality). In the TETROL/aniline/o-toluidine and TETROL/aniline/toluene mixed complexes comprising both favored (aniline) and disfavored (o-toluidine or toluene) guests, it is exclusively the former that are accommodated in the two hydrogen-bonding sites, while the third location, where hydrogen bonding with the host is absent, is able to contain both guest types. However, each of the three sites in the mixed complex containing only favored guests (TETROL/aniline/p-toluidine) is able to clathrate both species. These observations explain the increased site occupancy factors of preferred guests in the crystal and hence the selectivity of the host.

中文翻译：

氢键作用，是TETROL的两种溶剂混合配合物（包括邻位苯胺和邻位甲苯）的主体选择性提高的驱动力。

在这项工作中，我们表明，在包含主体（+）-（2 R，3 R）-1,1,4,4-四苯基丁烷-1,2， 3,4-四醇（TETROL）和来宾苯胺，甲苯和甲苯胺。竞争实验提供的主机选择性顺序，p -甲苯胺>苯胺>米-甲苯胺> ö甲苯胺>甲苯和，另外，含有三个结晶2 -客体复合物混合的苯胺/ ø甲苯胺，苯胺/ p-甲苯胺和苯胺/甲苯；总体上，主机与访客的比例为2：3。晶体衍射实验表明主体堆积是一致的同构。此外，不对称单元中的三个客体中只有两个与氢键合。第三者即使具有氢键能力（例如，氨基官能团）也不会经历这种相互作用类型。在TETROL /苯胺/邻甲苯胺和TETROL /苯胺/甲苯混合的复合物中，既包含有利的（苯胺）又包含不利的（o-甲苯（甲苯）或甲苯）客体，仅前者容纳在两个氢键位中，而第三个位置不存在与主体氢键的客体，可以包含两种客体类型。但是，混合复合物中的三个位点中，每个位点仅包含受惠的客体（TETROL /苯胺/对甲苯胺）都可以包容这两个物种。这些观察结果解释了晶体中优选客体的增加的位占据因子，并因此解释了宿主的选择性。

更新日期：2018-04-20

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