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 beta-cyclodextrin.

Cao Yujuan, Lu Runhua

Department of Chemistry and Environment, South China Normal University, Guangzhou 510006, PR China. caoyj@scnu.edu.cn

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2009 Aug 15

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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 (1)H NMR method in D(2)O/CD(3)OD 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.

Citation

Cao Yujuan, Lu Runhua. 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 beta-cyclodextrin. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2009 Aug 15;73(4):713-8