Does Perdeuteration Increase the Polarity of Janus Face Cycloalkanes?
Does Perdeuteration Increase the Polarity of Janus Face Cycloalkanes?
复制标题
全氘化是否会增加 Janus Face 环烷烃的极性？
DOI：
10.1002/hlca.202200177
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发表时间：
2023
影响因子：
1.8
通讯作者：
Fang Z
中科院分区：
文献类型：
--
作者：
Fang Z
受已故教授杰克·D. Dunitz的研究发现，全氘代Janus面环烷烃可能比其未标记形式的极性更强，因此制备了所有顺式-1，2，3，4，5，6-六氟环己烷（[2 H6]-1a）和所有顺式-1，2，3，4-四氟环戊烷（[2 H6]-3a）的氘代同位素体。在B3 LYP-D3水平上的计算表明，[2 H6]-1的极性并不比它的质子形式1更强，然而全氘代环戊烷[2 H6]-3的极性可能确实比3更强，尽管预测的幅度很小。尽管如此，在反相GC/MS柱上对3和[2 H6]-3龙舌兰混合物的保留时间分析表明，在未标记化合物之前检测到了全氘代同位素体3a，这与全氘代相关的极性增加一致。
Stimulated by a suggestion of the late ProfessorJack D. Dunitz, that perdeuterated Janus face cycloalkanes may be more polar than their unlabelled forms, the deuterated isotopologue of all cis‐1,2,3,4,5,6‐hexafluorocyclohexane ([2H6]‐1a) and all cis‐1,2,3,4‐tetrafluorocyclopentane ([2H6]‐3a) were prepared. Computation at the B3LYP−D3 level indicated that [2H6]‐1ais not more polar than its protio form 1, however perdeuterated cyclopentane [2H6]‐3amay indeed be more polar than3, although the magnitude is predicted to be small. None‐the‐less retention time analysis on a reverse phase GC/MS column of an add‐mix of3and [2H6]‐3agave some indication that the per‐deuterated isotopologue3awas detected marginally before the unlabelled compound consistent with increased polarity associated with perdeuteration.