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Molecular inclusion of PCB126 by beta-cyclodextrin: a combined molecular dynamics simulation and quantum chemical study

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Abstract

The effective enrichment and identification of lowly concentrated polychlorinated biphenyls (PCBs) in the environment is attracting much research attention due to human health concerns raised from their emissions. Cyclodextrins (CDs) are known to be capable to form inclusion complexes with a variety of organic molecules. The purpose of this study is to provide theoretical evidences whether CDs can form energetically stable inclusion complexes with PCBs through a host–guest interaction, and if so, whether infrared and Raman techniques are suitable for the detection of CD-modified PCBs. Focusing on a representative PCB molecule, 3,3′,4,4′,5-pentachlorobiphenyl (PCB126), we studied its molecular inclusion by β-CD (BCD) by performing molecular dynamics simulations and density functional theory calculations. Calculated results show that PCB126 and BCD preferentially form the stable 1:1 inclusion complex. The calculated IR spectra of the 1:1 inclusion complexes mainly present the spectra features of BCD and give only a slight indication for bands of the guest molecule. In contrast, the characteristic vibration modes of the guest molecule are remarkably prominent in the Raman spectra of the inclusion complexes. Based on the present results, we propose that BCD can potentially serve as a candidate for including PCB126 to form the stable 1:1 host–guest complex, and that Raman spectroscopy technology is expected to be suitable for the identification of the CD-modified PCBs, whereas IR spectroscopy is not feasible for such an application.

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Acknowledgments

This work is jointly supported by National Basic Research Program of China (973 Program 2007CB936602), National Natural Science Foundation of China (NSFC 20873076, 21075077), and Shandong Provincial Natural Science Foundation for Distinguished Young Scholar (JQ201004).

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  1. Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, Institute of Theoretical Chemistry, Shandong University, Jinan, 250100, People’s Republic of China

    Peng Liu, Hao Xu, Dongju Zhang & Jinhua Zhan

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  1. Peng Liu
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Correspondence to Dongju Zhang or Jinhua Zhan.

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Liu, P., Xu, H., Zhang, D. et al. Molecular inclusion of PCB126 by beta-cyclodextrin: a combined molecular dynamics simulation and quantum chemical study. J Incl Phenom Macrocycl Chem 76, 301–309 (2013). https://doi.org/10.1007/s10847-012-0199-4

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