高等学校化学学报

高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (2): 218.

• 研究论文 • 上一篇    下一篇

竞争包结法研究β-环糊精及其两种衍生物对一些手性脂肪族客体分子的识别作用

尤长城, 赵彦利, 刘育   

  1. 南开大学化学系, 天津 300071
  • 收稿日期:2000-05-08 出版日期:2001-02-24 发布日期:2001-02-24
  • 通讯作者: 刘　育(1954年出生),男,博士,教授,博士生导师,主要从事主2客体化学和超分子化学研究.
  • 基金资助:

    国家自然科学基金(批准号:29972029);国家杰出青年科学基金(批准号:29625203);天津市自然科学基金资助

Molecular Recognition Study ofβ-Cyclodextrin and Its Two Derivatives with Some Aliphatic Guests by Competitive Inclusion Method

YOU Chang-Cheng, ZHAO Yan-Li, LIU Yu   

  1. Department of Chemistry, Nankai University, Tianjin 300071, China
  • Received:2000-05-08 Online:2001-02-24 Published:2001-02-24

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摘要： 以酚酞作为光谱探针,采用紫外可见光谱滴定法测定了β-环糊精(β-CD)、单(6-氧α-麦芽糖)-β-环糊精(6-G2-β-CD)和单[2-氧(2-羟丙基)]-β环糊精(2HP-β-CD)在25℃时,pH=10.5缓冲液中(0.025mol/L)与几种脂肪族手性客体分子所形成超分子配合物的稳定常数.结果表明,多种弱相互作用力协同作用于环糊精的配位过程,主客体间的尺寸匹配决定所形成配合物的稳定性.环糊精衍生物的取代基影响主体的配位能力,对于尺寸较小的客体分子配位能力的大小一般为2-HP-β-CD>β-CD>-6-G2-β-CD.另一方面,3种环糊精主体化合物对一些脂肪族客体分子也表现出一定的手性识别能力,对(+)异构体给出相对较强的键合能力,其中,2-HP-β-CD对(+)/(-)樟脑的配位选择性为1.25.

关键词: &beta, -环糊精, 酚酞, 脂肪醇, 竞争包结, 分子识别

Abstract: Spectrophotometric titrations were performed in aqueous buffer solution(pH=10.5, c=0.025 mol/L) at 25 ℃ to determine the binding constants ofβ-cyclodextrin(β-CD), mono(6-O-α-maltosyl)-β-cyclodextrin(6-G2-β-CD) and mono[2-O-(2-hydroxypropyl)]-β-cyclodextrin(2-HP-β-CD) with several aliphatic chiral guest molecules using phenolphthalein as a spectral probe. The results obtained indicate that several weak interactions cooperatively contribute to the inclusion complexation of theβ-cyclodextrin hosts and the complex stability is dominated by the size/shape-matching between host and guest. The substituent on the cyclodextrin derivatives changes its original binding ability. For the relatively small guest molecules,i.e., borneol, camphor and menthol, the molecular binding ability is 2-HP-β-CD>β-CD>6-G2-β-CD. Furthermore, the threeβ-cyclodextrin hosts can also serve as chiral discrimination reagents and afford stronger binding ability toward (+)-isomers. Among them, 2-HP-β-CDgives a moderate enantiometric selectivity of 1.25 for (+)/(-)-camphor.

Key words: β-Cyclodextrin, Phenolphthalein, Aliphatic alcohol, Competitive inclusion, Molecular recognition

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