Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

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• 作者：Min Ying Tsang ; Florencia Di Salvo ; Francesc Teixidor ; Clara Vi帽as ; Jos茅 Giner Planas ; Duane Choquesillo-Lazarte ; Nicolas Vanthuyne
• 刊名：Crystal Growth & Design
• 出版年：2015
• 出版时间：February 4, 2015
• 年：2015
• 卷：15
• 期：2
• 页码：935-945
• 全文大小：767K
• ISSN：1528-7505

文摘

Ten structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C₂B₁₀H₁₀; rac-1a) or m-carborane (1,7-closo-C₂B₁₀H₁₀; rac-2a) or p-carborane (1,7-closo-C₂B₁₀H₁₀; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C₆H₅; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O鈥揌路路路N hydrogen bonded homochiral 2₁-helical networks, except that for rac-3a, which forms O鈥揌路路路N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols鈥攅ither in racemic or enantiopure forms鈥攖hat form O鈥揌路路路N hydrogen bonded homochiral 2₁-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state.