Synthesis and crystallographic studies of disubstituted carboranyl alcohol derivatives: prevailing chiral recognition?

Di Salvo, Florencia, Paterakis, Christos, Tsang, Min Ying, García, Yolanda, Viñas, Clara, Teixidor, Francesc, Giner Planas, José, Light, Mark E., Hursthouse, Michael B. and Choquesillo-Lazarte, Duane (2013) Synthesis and crystallographic studies of disubstituted carboranyl alcohol derivatives: prevailing chiral recognition? Crystal Growth & Design, 13 (4), 1473-1484. (doi:10.1021/cg400082z).

Abstract

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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Contributors

Author: Mark E. Light

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