Ionic hydrogen bonding between arginine side chain and nucleic acid bases

Lei Li, Cuiying Huang, Xiaonan Jiang, Xichan Gao, Changsheng Wang

Research output: Contribution to journalArticlepeer-review


The optimal structures of twenty-two hydrogen-bonded complexes composed of one charged arginine side chain molecule and one nucleic acid base in gas phase were obtained at the MP2/6-31+G(d,p) level. The binding energies in gas phase were evaluated at the MP2/aug-cc-pVTZ level including basis set superposition error (BSSE) correction. The optimal structures for these hydrogen-bonded complexes in water solvent were further obtained by using PCM model combined with the MP2/6-31+G(d,p) method. The binding energies in water solvent were evaluated by using PCM model combined with the MP2/aug-cc-pVTZ method. It is found that the ionic hydrogen bonding strength between the arginine side chain and one of the five nucleic acid bases highly correlates to the charge transfer between the two monomers, the electron density at the hydrogen bond critical point, and the second-order stabilization energy. Compared to the neutral hydrogen bond, the ionic hydrogen bond exhibits more significant covalent character. It is also found that the stability of the hydrogen-bonded complexes can be predicted according to the enthalpy change of the protonation reaction of the nucleic acid bases. The more negative the enthalpy change of the protonation reaction, the more stable the hydrogen-bonded complexes.

Original languageEnglish
Pages (from-to)1460-1467
Number of pages8
JournalKao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities
Issue number8
Publication statusPublished - 2016 Aug 10


  • Arginine side chain
  • Binding energy
  • Enthalpy change of protonation reaction
  • Ionic hydrogen bond
  • Nucleic acid base


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