Chinese Science Bulletin

, Volume 57, Issue 16, pp 1964–1971 | Cite as

Theoretical characterization of electronic structures and properties of C-F···H-C pseudohydrogen bonds

  • Kun YuanEmail author
  • YanZhi Liu
  • LingLing Lü
  • GuoFang Zuo
  • YuanCheng Zhu
  • XiaoNing Dong
Open Access
Article Physical Chemistry


The weak intermolecular interactions between 2-F-tetrahydrofuran and imidazole, pyrimidine, adenine, and guanine were studied theoretically using density functional B3LYP/6-311++G** and HF/6-311++G** methods. The results showed that both conventional N...H hydrogen bond and C-F...H-C pseudohydrogen bond (PHB) structures coexist in the four complexes. The weak intermolecular interaction energies indicate that the relative stabilities of the four complexes are in the order guanine...F > imidazole ...F > adenine...F > pyrimidine...F. The characteristics of the four PHBs were determined using geometry optimizations, stretching vibrational frequencies, and natural bond orbital and electron density topological properties calculations. The most important result is that the F group of 2-F-tetrahydrofuran can activate the C-H to accept electrons from another molecule, and C-F...H-C PHB formation is relatively favorable.


weak interaction pseudohydrogen bond electronic structure electron density topological property 


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© The Author(s) 2012

Open AccessThis article is distributed under the terms of the Creative Commons Attribution 2.0 International License (, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Authors and Affiliations

  • Kun Yuan
    • 1
    • 2
    Email author
  • YanZhi Liu
    • 1
    • 2
  • LingLing Lü
    • 1
    • 2
  • GuoFang Zuo
    • 1
    • 2
  • YuanCheng Zhu
    • 1
    • 2
  • XiaoNing Dong
    • 1
    • 2
  1. 1.College of Life-science and ChemistryTianshui Normal UniversityTianshuiChina
  2. 2.Key Laboratory for New Molecular Materials Design and Function of Gansu Education DepartmentTianshuiChina

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