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Fluorinated Aminopyridines: Synthesis, Structure, and Rare Liquid–Liquid Cocrystal Formation Driven by Unusually Short N–H···F–C Hydrogen Bonding
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2020-06-16 , DOI: 10.1021/acs.cgd.0c00689
Andrew J. Peloquin 1 , Daniel A. Kure 2 , Abby R. Jennings 2 , Colin D. McMillen 1 , Scott T. Iacono 2 , William T. Pennington 1
Affiliation  

The role of hydrogen bonding in the crystal packing of a series of 4-aminoperfluoropyridines was studied using single-crystal X-ray crystallography. The aminoperfluoropyridines were synthesized using only excess amine to serve as both nucleophile and base. Instead of addition to the perfluoropyridine ring, a strong N–H···F–C hydrogen bond led to cocrystal formation of perfluoropyridine with sterically hindered amines dicyclohexylamine as well as 2-methylpiperdine. This formation is, to our knowledge, the first report of two nonreacting liquids, consisting of only discrete small molecules, combining to form a cocrystalline solid stable under ambient conditions. Perfluoropyridine is stabilized in the crystal lattice approximately 100 °C above its normal boiling point.

中文翻译:

氟化氨基吡啶:由异常短的NH····FC氢键驱动的合成,结构和罕见的液-液共晶体形成

使用单晶X射线晶体学研究了氢键在一系列4-氨基全氟吡啶晶体包装中的作用。仅使用过量的胺作为亲核试剂和碱来合成氨基全氟吡啶。除了加到全氟吡啶环上之外,强大的N–H···F–C氢键导致全氟吡啶与位阻胺二环己胺以及2-甲基哌啶共晶形成。据我们所知,这种形成是两种非反应性液体的首次报道,这两种液体仅由离散的小分子组成,结合形成在环境条件下稳定的共结晶固体。全氟吡啶在高于其正常沸点约100°C的晶格中稳定。
更新日期:2020-08-05
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