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Citation: ZHAO Jun, ZHENG Ming-Xian, LIN Yi-Ji, CHEN Yuan-Chuan, RUAN Yuan-Ping, ZHANG Hui. Inclusion Resolution of 1,1'-Bi-2-naphthol: Crystal Structure and CD Spectroscopy of the Inclusion Complexes[J]. Acta Physico-Chimica Sinica, ;2010, 26(07): 1832-1836. doi: 10.3866/PKU.WHXB20100633 shu

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

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 Date: 2 February 2010
Available Online: 6 May 2010

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