Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (07): 1832-1836.doi: 10.3866/PKU.WHXB20100633

• STRUCTURE CHEMISTRY • Previous Articles     Next Articles

Inclusion Resolution of 1,1'-Bi-2-naphthol: Crystal Structure and CD Spectroscopy of the Inclusion Complexes

ZHAO Jun, ZHENG Ming-Xian, LIN Yi-Ji, CHEN Yuan-Chuan, RUAN Yuan-Ping, ZHANG Hui   

  1. State Key Laboratory of Physical Chemistry of Solid Surfaces, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China
  • Received:2010-02-02 Revised:2010-03-25 Published:2010-07-02
  • Contact: ZHANG Hui E-mail:huizhang@xmu.edu.cn

Abstract:

A highly efficient and environmentally friendly method for the resolution of racemic 1,1'-bi-2-naphthol (BINOL) was developed by inclusion complexation with the cheap and readily accessible (R)/(S)-N,N,N-trimethyl-1-hydroxyl-3-methyl-2-butanaminiumiodide resolving agents, which were prepared by a simple two-step reaction starting with D/L-valinol. The X-ray structural analysis was carried out for the inclusion complex of the (R)-quaternary ammoniumsalt with (R)-BINOL in CH3OH. This showed that the O—H…I- hydrogen bonds among the bridged iodide anions with the alcoholic hydroxyl of the host (resolving agent) and the phenolic hydroxyls of the guests (BINOL) together with the C—H…O hydrogen-bond interactions between the host and guest molecules from the adjacent layers are responsible for the chiral recognition in the inclusion complex formation. In addition, the solution and solid-state circular dichiroism(CD) spectra of a pair of inclusion complexes were also carefully investigated.

Key words: Circular dichiroismspectroscopy, 1,1'-Bi-2-naphthol, Inclusion resolution, (R)/(S)-N,N,N-Trimethyl-1-hydroxyl-3-methyl-2-butanaminiumiodide, Crystal structure

MSC2000: 

  • O641.6