Increasing the structural boundary of quasiracemate formation: 4-substituted naphthylamides
Increasing the structural boundary of quasiracemate formation: 4-substituted naphthylamides
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DOI：
10.1039/d0ce01331e
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发表时间：
2021-01-07
期刊：
影响因子：
3.1
通讯作者：
Wheeler, Kraig A.
中科院分区：
文献类型：
--
作者：
Craddock, Drew E.;Parks, McKenzie J.;Wheeler, Kraig A.
瓜西外消旋体——由成对的近对映体组成的材料——形成模仿其外消旋对应物观察到的反转关系的晶体图案。我们小组最近的研究探索了一系列手性（N-苯甲酰）甲基苄胺，以了解共结晶的结构边界。这项研究将这些早期研究扩展到包括萘酰胺准外消旋体，其分子框架与之前的二芳基酰胺相比，体积大约大 20%。制备了一系列萘酰胺，其中侧链官能团的大小逐渐不同（即，H 至 C6H5），以产生 55 种可能的独特外消旋和准外消旋组合对。使用 X 射线晶体学、热分析方法和晶格能计算从这些材料收集的数据为了解空间上更大的萘酰胺分子框架如何在准对映异构体的成对组装过程中促进取代基更大的结构变化提供了重要的见解。
Guasiracemates - materials consisting of pairs of near enantiomers - form crystalline motifs that mimic the inversion relationships observed for their racemic counterparts. Recent investigations from our group explored a family of chiral (N-benzoyt)methylbenzylamines to understand the structural boundary of cocrystallization. This investigation extends these earlier studies to include naphthylamide quasiracemates, where the molecular framework is similar to 20% larger by volume than the previous diarylamides. A family of naphthylamides was prepared where the pendant functional group differs incrementally in size (i.e., H to C6H5) to give 55 possible unique pairs of racemic and quasiracemic combinations. Data collected from these materials using X-ray crystallography, thermal analysis methods and lattice energy calculations offer important insight into how a spatially larger naphthylamide molecular framework promotes greater structural variance of substituents during the pairwise assembly of quasienantiomers.