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Density functional theory study of the potassium complexation of an unsymmetrical 1,3-alternate calix[4]-crown-5-N-azacrown-5 bearing two different crown rings

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Abstract

Theoretical studies of an unsymmetrical calix[4]-crown-5-N-azacrown-5 (1) in a fixed 1,3-alternate conformation and the complexes 1·K+(a), 1·K+(b), 1·K+(c) and 1·K+K+ were performed using density functional theory (DFT) at the B3LYP/6-31G* level. The fully optimized geometric structures of the free macroligand and its 1:1 and 1:2 complexes, as obtained from DFT calculations, were used to perform natural bond orbital (NBO) analysis. The two main types of driving force metal–ligand and cation–π interactions were investigated. NBO analysis indicated that the stabilization interaction energies (E 2) for O…K+ and N…K+ are larger than the other intermolecular interactions in each complex. The significant increase in electron density in the RY* or LP* orbitals of K+ results in strong host–guest interactions. In addition, the intermolecular interaction thermal energies (ΔE, ΔH, ΔG) were calculated by frequency analysis at the B3LYP/6-31G* level. For all structures, the most pronounced changes in the geometric parameters upon interaction are observed in the calix[4]arene molecule. The results indicate that both the intermolecular electrostatic interactions and the cation–π interactions between the metal ion and π orbitals of the two pairs that face the inverted benzene rings play a significant role.

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Acknowledgments

The author wish to acknowledge financial support from the Scientific Research Fund of the Hunan Provincial Education Department (No. 09A091) for this research work.

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Authors and Affiliations

  1. Key Laboratory of Environmentally Friendly Chemistry, College of Chemistry, Xiangtan University, Xiangtan, Hunan, 411105, People’s Republic of China

    Xiaoyan Zheng, Xueye Wang, Keqi Shen, Yuan Miao & Dan Ouyang

  2. Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan, 411105, People’s Republic of China

    Xiaoyan Zheng, Xueye Wang, Keqi Shen, Yuan Miao & Dan Ouyang

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  1. Xiaoyan Zheng
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  2. Xueye Wang
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  3. Keqi Shen
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  4. Yuan Miao
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  5. Dan Ouyang
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Correspondence to Xueye Wang.

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Zheng, X., Wang, X., Shen, K. et al. Density functional theory study of the potassium complexation of an unsymmetrical 1,3-alternate calix[4]-crown-5-N-azacrown-5 bearing two different crown rings. J Mol Model 17, 2659–2668 (2011). https://doi.org/10.1007/s00894-010-0945-8

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  • DOI: https://doi.org/10.1007/s00894-010-0945-8

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