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Highly Selective Fluoride Recognition by a Small Tris-Urea Covalent Cage
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-24 , DOI: 10.1021/acs.joc.9b03429 Magalie Delecluse 1 , Cédric Colomban 1 , Bastien Chatelet 1 , Sabine Chevallier-Michaud 1 , Delphine Moraleda 1 , Jean-Pierre Dutasta 2 , Alexandre Martinez 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-24 , DOI: 10.1021/acs.joc.9b03429 Magalie Delecluse 1 , Cédric Colomban 1 , Bastien Chatelet 1 , Sabine Chevallier-Michaud 1 , Delphine Moraleda 1 , Jean-Pierre Dutasta 2 , Alexandre Martinez 1
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A highly selective recognition of fluoride was achieved through the design of a small hemicryptophane cage (3) presenting a southern tris-urea hosting moiety. The resulting host–guest complex has been characterized by electrospray ionization-high-resolution mass spectrometry, 1H and 19F NMR, and X-ray diffraction techniques. In particular, X-ray diffraction analysis of [3·F–] reveals that the encapsulation of one fluoride, within 3, occurs through NH···F– H-bonding with the six NH residues of the tris-urea ligand. An association constant of 1200 M–1 was extracted from 1H NMR titration experiments, indicating that efficient fluoride binding also occurs in solution. Finally, in sharp contrast with previously reported urea-based hemicryptophane hosts, the small preorganized cavity found in 3 allows for an exclusive selectivity for fluoride over other competing halides.
中文翻译：
Tris-尿素共价笼子对氟的高度选择性识别
氟化物的高度选择性识别是通过设计一个呈现南三聚脲宿主部分的小半隐笼（3）实现的。通过电喷雾电离高分辨率质谱，1 H和19 F NMR以及X射线衍射技术对所得的主客体复合物进行了表征。尤其是，[ 3 ·F – ]的X射线衍射分析显示，3中的一种氟化物的包封是通过NH···F – H与三脲脲配体的六个NH残基键合而发生的。从1中提取了1200 M –1的缔合常数1 H NMR滴定实验表明溶液中也发生了有效的氟化物结合。最后，与先前报道的基于尿素的半色氨酸宿主形成鲜明对比的是，在3中发现的小的预组织空腔使得氟化物对其他竞争性卤化物具有排他性选择性。
更新日期：2020-03-24
中文翻译：
Tris-尿素共价笼子对氟的高度选择性识别
氟化物的高度选择性识别是通过设计一个呈现南三聚脲宿主部分的小半隐笼（3）实现的。通过电喷雾电离高分辨率质谱，1 H和19 F NMR以及X射线衍射技术对所得的主客体复合物进行了表征。尤其是，[ 3 ·F – ]的X射线衍射分析显示，3中的一种氟化物的包封是通过NH···F – H与三脲脲配体的六个NH残基键合而发生的。从1中提取了1200 M –1的缔合常数1 H NMR滴定实验表明溶液中也发生了有效的氟化物结合。最后，与先前报道的基于尿素的半色氨酸宿主形成鲜明对比的是，在3中发现的小的预组织空腔使得氟化物对其他竞争性卤化物具有排他性选择性。
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