The Chiral Trimer and a Metastable Chiral Dimer of Achiral Hexafluoroisopropanol: A Multi‐Messenger Study,Angewandte Chemie International Edition

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The Chiral Trimer and a Metastable Chiral Dimer of Achiral Hexafluoroisopropanol: A Multi‐Messenger Study
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-03-08 , DOI: 10.1002/anie.201813881
Sönke Oswald ₁ , Nathan A. Seifert ₂ , Fabian Bohle ₃ , Maxim Gawrilow ₁ , Stefan Grimme ₃ , Wolfgang Jäger ₂ , Yunjie Xu ₂ , Martin A. Suhm ₁

Affiliation

1,1,1,3,3,3‐hexafluoro‐propan‐2‐ol aggregates preferentially into an achiral dimer of achiral monomers, but the trimer is found to prefer three metastable chiral monomer units arranged into a strained OH⋅⋅⋅O hydrogen‐bonded ring, which is reinforced by secondary CH⋅⋅⋅FC interactions. This is shown by a combination of infrared, microwave, and Raman spectroscopy in supersonic jet expansions and supported by high‐level quantum chemical calculations. It involves an activation of the monomers by >15 kJ mol⁻¹, clearly driven by the much stronger hydrogen‐bond interaction available to the gauche and even more to the cis monomer units.

中文翻译：

手性六氟异丙醇的手性三聚体和亚稳手性二聚体：多信使研究

1,1,1,3,3,3-六氟丙烷-2-醇优先聚集到非手性单体的非手性二聚体中，但发现三聚体更喜欢三个亚稳的手性单体单元，它们被排列成应变的OH⋅⋅⋅O氢键环，可通过二次CH⋅·⋅FC相互作用得到增强。超音速射流膨胀中红外，微波和拉曼光谱的结合证明了这一点，并得到了高级量子化学计算的支持。它涉及到单体的活化> 15 kJ mol ^-1，这显然是由薄纱和甚至更多的顺式单体单元更强的氢键相互作用所驱动的。

更新日期：2019-03-08

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