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 1a, 3-pyridyl 1b, 4-pyridyl 1c, 2-quinolyl 1d, 4-quinolyl 1e, phenyl 1f) 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 1b. The crystal structures of the meso compounds syn-1a路2MeOH, syn-1b, syn-1f路0.25H2O and racemic anti-1a路MeOH, anti-1a路EtOH, and anti-1d路2H2O 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).