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

MIN YING TSANG; FLORENCIA DI SALVO; FRANCESC TEIXIDOR; CLARA VIÑAS; JOSÉ GINER PLANAS; DUANE CHOQUESILLO-LAZARTE; NICOLAS VANTHUYNE

CRYSTAL GROWTH & DESIGN

AMER CHEMICAL SOC

Lugar: Washington; Año: 2015 vol. 2005 p. 1033 - 1040

1528-7483

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 pcarborane (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 Xray crystallography. All racemic and enantiopure structures show O−H???N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O−H???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either in racemic or enantiopure formsthat form O−H???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.