摘要
以D/L-缬氨醇为原料,通过二步反应得到价廉易得的拆分剂碘化(R)/(S)-N,N,N-三甲基-1-羟基-3-甲基-2-丁铵,采用包结拆分法,成功实现了对1,1′-联-2-萘酚(BINOL)的拆分.对具有(R)-构型的季铵盐与(R)-BINOL在甲醇中所形成包结物的晶体结构分析结果表明:I-离子桥联主体(拆分剂)的醇羟基和客体(BINOL)的酚羟基形成O-H…I-氢键,以及相邻层的主客体分子之间的C-H…O氢键相互作用是在包结物中实现手性识别的关键.同时对两个包结物的溶液和固体圆二色(CD)光谱进行了研究.
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-butanaminium iodide 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 ammonium salt 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 vips （BINOL） together with the C-H… O hydrogen-bond interactions between the host and vip 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.
出处
《物理化学学报》
SCIE
CAS
CSCD
北大核心
2010年第7期1832-1836,共5页
Acta Physico-Chimica Sinica
基金
国家自然科学基金(20773098,20973136)
广西化工研究院资助项目~~
