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

Florencia Di Salvo, Christos Paterakis, Min Ying Tsang, Yolanda García, Clara Viñas, Francesc Teixidor, José Giner Planas*, Mark E. Light, Michael B. Hursthouse, and Duane Choquesillo-Lazarte

 

Cryst. Growth Des., 2013, 13 (4), pp 1473–1484

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·2MeOH, syn-1b, syn-1f·0.25H2O and racemic anti-1a·MeOH, anti-1a·EtOH, and anti-1d·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–H···N and/or O–H···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).

 

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