Synthesis and Dimerization Properties of Cup‐ and Bowl‐shaped Cyclic Trilactams,Asian Journal of Organic Chemistry

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Synthesis and Dimerization Properties of Cup‐ and Bowl‐shaped Cyclic Trilactams
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-04-01 , DOI: 10.1002/ajoc.202000140
Sitanan Sartyoungkul ₁ , Yumi Yakiyama ₁ , Hidehiro Sakurai ₁

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Two chiral trilactams, cup‐shaped (−)‐1 and bowl‐shaped (−)‐2 , were synthesized. Single crystal X‐ray analysis revealed that (−)‐1 formed dimer structure by the formation of three NH⋅⋅⋅O type complementary hydrogen bonds at three amide moieties. The equilibrium constant (K _eq) and kinetic parameters ▵H ° and ▵S ° of the dimer formation phenomenon of (−)‐1 were determined by variable temperature proton NMR. Further binding energy calculation on both (−)‐1 and (−)‐2 dimers confirmed the more favourable formation of (−)‐1 dimer than (−)‐2 dimer, explaining the significant solubility difference of the two against the less polar solvent, such as CHCl₃. Trilactam (−)‐1 afforded coordination polymer by complexation with Zn²⁺, keeping the capsule‐like structure.

中文翻译：

杯形和碗形环状三内酰胺的合成和二聚性质

合成了两个手性三内酰胺，杯形（-）- 1和碗形（-）- 2。单晶X射线分析表明（-）- 1通过在三个酰胺部分形成三个NH····O型互补氢键形成二聚体结构。平衡常数（ķ_当量）和动力学参数▵ ħ °和▵小号的二聚体形成现象°（ - ） - 1，通过变温质子NMR测定。对（−）- 1和（−）‐ 2二聚体的进一步结合能计算证实了（−）‐ 1二聚体比（−）‐ 2更有利的形成二聚体，解释了两者相对于极性较小的溶剂（如CHCl _3）的显着溶解度差异。Trilactam（-）- 1通过与Zn ²⁺络合提供配位聚合物，保持了胶囊状结构。

更新日期：2020-04-01

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