Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?

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• 作者：Florencia Di Salvo ; Christos Paterakis ; Min Ying Tsang ; Yolanda Garc铆a ; Clara Vi帽as ; Francesc Teixidor ; Jos茅 Giner Planas ; Mark E. Light ; Michael B. Hursthouse ; Duane Choquesillo-Lazarte
• 刊名：Crystal Growth & Design
• 出版年：2013
• 出版时间：April 3, 2013
• 年：2013
• 卷：13
• 期：4
• 页码：1473-1484
• 全文大小：597K
• 年卷期：v.13,no.4(April 3, 2013)
• ISSN：1528-7505

文摘

The syntheses of new o-carboranyldiols bearing aromatic rings bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl <b>1ab>, 3-pyridyl <b>1bb>, 4-pyridyl <b>1cb>, 2-quinolyl <b>1db>, 4-quinolyl <b>1eb>, phenyl <b>1fb>) are reported. The compounds are obtained as mixtures of meso (syn) and racemic (anti) stereoisomers with a slight diastereomeric excess (syn:anti ratio of 0.7:1) in all cases but in <b>1bb>. The crystal structures of the meso compounds syn<b>-1ab>路2MeOH, syn<b>-1bb>, syn<b>-1fb>路0.25Hb>2b>O and racemic anti<b>-1ab>路MeOH, anti<b>-1ab>路EtOH, and anti<b>-1db>路2Hb>2b>O are reported. We provide an analysis of these compounds by means of NMR and X-ray crystallography, in the context of crystal engineering and chiral recognition. The results show that the crystal packings for these alcohols are dominated by the supramolecular O鈥揌路路路N and/or O鈥揌路路路O hydrogen bonds. Supramolecular analysis of all compounds in this work reveals that homochiral self-assembly, that is, formation of homochiral hydrogen bonded complexes, prevails over heterochiral self-assembly (formation of heterochiral hydrogen bonded complexes).