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Acta Chimica Sinica >

2012 , Vol. 70 >Issue 12: 1347 - 1354

DOI: https://doi.org/10.6023/A1111211

Special Topic

Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation

  • Yi Pinggui ,
  • Liu Zhengjun ,
  • Wang Zhaoxu ,
  • Hou Bo ,
  • Yu Xianyong ,
  • Li Xiaofang
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  • Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Received date: 2011-11-21

  Revised date: 2012-04-20

  Online published: 2012-04-20

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172066, 20772027), Hunan Provincial Natural Science Foundation of China (Nos.10JJ4011, 11JJ2007), Scientific Research Fund of Hunan Provincial Education Department (No. 09K081).

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Abstract

The structures of 2-(3'-hydroxy-2'-pyridyl)benzoxazole (HPyBO) with alkali (or alkaline earth) metal ions (Li+, Na+, K+, Be2+, Mg2+ and Ca2+) were fully optimized at the 6-311++G(d,p) level by using B3LYP density functional theory and the binding energies were calculated at the same level. The result shows that the cation-π interaction between alkali (or alkaline earth) metal ions and HPyBO complexes are very strong, some of the interactions are even comparable to chemical bonding. The relative energies show that cation-π interaction can change the energy barrier of intramolecular proton transfer. When considering the solvent effect of water, the relative energies of isomers and the energy barrier of intramolecular proton transfer are changed to some extent. In addition, the properties at the BCPs (bond critical points) of intramolecular hydrogen bond in the complexes are also discussed.

Key words： density functional theory (DFT); cation-π interaction; intramolecular proton transfer; natural bond orbital (NBO); atoms in molecules (AIM)

Cite this article

Yi Pinggui , Liu Zhengjun , Wang Zhaoxu , Hou Bo , Yu Xianyong , Li Xiaofang . Alkali (Alkali Earth) Metal Ions with 2-(3'-Hydroxy-2'-pyridyl)benzoxazole Cation-π Complexes and Its Intramolecular Proton Transfer Process: A Theoretical Investigation[J]. Acta Chimica Sinica, 2012 , 70(12) : 1347 -1354 . DOI: 10.6023/A1111211

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