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Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes
Synthesis ( IF 2.6 ) Pub Date : 2020-01-13 , DOI: 10.1055/s-0039-1690785
Marvin Linnemannstöns , Beate Neumann , Hans-Georg Stammler , Norbert W. Mitzel 1
Affiliation  

Starting from trichloro(phenylethyl)silane, six differently fluorinated triaryl(phenylethyl)silanes were synthesized by salt elimination reactions and their structures were determined by X-ray diffraction analysis. Tris(pentafluorophenyl)(phenylethyl)silane reveals a folded structure due to intramolecular π-stacking interactions, while those with a lower degree of fluorination show either intermolecular π-stacking or no interplay between the aryl groups. A similar folded structure was observed for (4-methylphenethyl)tris(pentafluorophenyl)silane and [2-(naphth-2-yl)ethyl]tris(pentafluorophenyl)silane, both generated from the corresponding trichlorosilanes. In contrast, the inversely fluorinated [2-(pentafluorophenyl)ethyl]triphenylsilane only revealed intermolecular π-stacking interactions. Compounds with tetrafluoropyridyl substituents behave differently; with these compounds, π-stacking is only observed between the fluorinated units. All compounds were analyzed by NMR and IR spectroscopy, elemental analyses and single-crystal X-ray diffraction, and found to have strong H/C/N/F···F and N···C contacts.

中文翻译:

三芳基(苯乙基)硅烷的合成与结构多样性

从三氯(苯乙基)硅烷开始,通过盐消除反应合成了六种不同的氟化三芳基(苯乙基)硅烷,并通过X射线衍射分析确定了它们的结构。三(五氟苯基)(苯乙基)硅烷由于分子内π堆积相互作用而显示出折叠结构,而氟化程度较低的那些则显示出分子间π堆积或芳基之间没有相互作用。对于(4-甲基苯乙基)三(五氟苯基)硅烷和[2-(萘-2-基)乙基]三(五氟苯基)硅烷观察到相似的折叠结构,两者均由相应的三氯硅烷产生。相反,反向氟化的[2-(五氟苯基)乙基]三苯基硅烷仅显示出分子间的π-堆积相互作用。具有四氟吡啶基取代基的化合物的行为不同;对于这些化合物,仅在氟化单元之间观察到π堆积。通过NMR和IR光谱,元素分析和单晶X射线衍射分析所有化合物,发现它们具有强的H / C / N / F··F和N··C接触。
更新日期:2020-01-14
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