1H NMR titration and quantum calculation for the inclusion complexes of cis-cyclooctene, cis, cis-1, 3-cyclooctadiene and cis, cis-1, 5-cyclooctadiene with β-cyclodextrin

被引：12

作者：

Cao Yujuan ^{[1
,3
]}

Lu Runhua ^{[2
]}

机构：

[1] S China Normal Univ, Dept Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China

[2] China Agr Univ, Coll Sci, Dept Appl Chem, Beijing 100094, Peoples R China

[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China

来源：

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2009年 / 73卷 / 04期

关键词：

beta-Cyclodextrin; Cyclooctene; Cyclooctadiene; H-1 NMR spectroscopy; Quantum calculation; ENANTIODIFFERENTIATING PHOTOISOMERIZATION; ALPHA-CYCLODEXTRIN; SUPRAMOLECULAR PHOTOCHIROGENESIS; NMR INVESTIGATIONS; DERIVATIVES; CHEMISTRY; CONSTANTS;

D O I：

10.1016/j.saa.2009.03.012

中图分类号：

O433 [光谱学];

学科分类号：

0703 ; 070302 ;

摘要：

The inclusion behavior of cis-cyclooctene, cis, cis-1, 3-cyclooctadiene and cis, cis-1, 5-cyclooctadiene with beta-cyclodextrin (beta-CD) was studied by using H-1 NMR method in D-2/CD3OD solution and PM3 quantum-chemical simulation in vacuum. The experimental results indicate that each guest molecule penetrates deeply into beta-CD cavity and forms equimolecular inclusion complex with the host. The association constants of the complexes were determined by non-linear least-square method on the bases of the conversion-dependent chemical shift of two protons of the host molecule. The inclusion process and the most probable structure of the inclusion complexes were simulated using PM3 energy scanning and optimization. The trend of stability of the three inclusion complexes deduced from their calculated stabilization energies agrees well with the order of their association constants obtained from NMR experiments. (C) 2009 Elsevier B.V. All rights reserved

引用

页码：713 / 718

页数：6

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