A Protonated Quinone Methide Stabilized by a Combination of Partial Aromatization and π-Interaction: Spectroscopic and Crystallographic Analysis
A Protonated Quinone Methide Stabilized by a Combination of Partial Aromatization and π-Interaction: Spectroscopic and Crystallographic Analysis
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通过部分芳构化和γ-相互作用相结合稳定质子化醌甲基化物：光谱和晶体分析
DOI：
10.1021/acs.joc.9b00923
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Lectka, Thomas
中科院分区：
文献类型：
--
作者：
Kazim, Muhammad;Siegler, Maxime A.;Lectka, Thomas
我们扩展了阳离子−π相互作用的范围，使之包括了一个由π-叠层对苯醌甲基化物（p-QM）质子化产生的碳正离子−π系统。这种不寻常的碳正离子通过QM部分的部分芳构化和与相邻芳环的π-系统的空间相互作用的组合来稳定。质子化形式的单晶X射线分析揭示了由涉及两个前体分子和一个质子的氢结合复合物组成的结构。
We have expanded the repertoire of cation−π interactions to include a carbocation−π system resulting from the protonation of a π-stackedpara-quinone methide (p-QM). This unusual carbocation is stabilized by a combination of partial aromatization of the QM moiety and through-space interaction with the π-system of the adjacent aromatic ring. Single crystal X-ray analysis of the protonated form reveals a structure consisting of a hydrogen-bound complex involving two molecules of the precursor and one proton.