Chiral 3,3′-disubstituted BINOL derivatives: Syntheses, characterizations and X-ray structure analyses

✍ Scribed by Guo-Hua Liu; Yun-Ning Xue; Mei Yao; Hai-Bing Fang; Han Yu; Shi-Ping Yang

• Publisher: Elsevier Science
• Year: 2008
• Tongue: English
• Weight: 852 KB
• Volume: 875
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2007.03.057

✦ Synopsis

Two chiral 3,3 0 -disubstituted BINOL derivatives 3a and 3b have been synthesized and their crystal structures have been reported. Their direct evidence of the solid-state conformations and their structural details of the unique 2D supramolecular architectures have been obtained. The intramolecular hydrogen bonds of both compounds lock two substituents at 3,3 0 -positions (like two arms) towards exterior around naphthyl backbones in an extended conformations. In the (R)-3a crystals, the uniform hand-to-hand intermolecular hydrogen bonds of OAHAN link the adjacent molecules into the infinite chainlike structure, and the p-p stacking interactions and the inter-aggregate Cl/Cl close connections result in forming the higher-order 2D supramolecular crossbedded self-adhesive architecture. For (R)-3b, the structural characteristics of the self-assembly is to form supramolecular crossbedded self-adhesive structure through the cooperative hydrogen bonding.