pi-Stacked Quadruply Hydrogen-Bonded Dimers: pi-Stacking Influences H-Bonding

D. Guo, H. Zuilhof, R.P. Sijbesma

Research output: Contribution to journalArticleAcademicpeer-review

53 Citations (Scopus)


The effects of pi-stacking on the stability of multiply hydrogen-bonded systems are investigated using hybrid DFT calculations on pi-stacked quadruply H-bonded dimers of ureidopyrimidinone in its different tautomeric forms. Both the strengths of the hydrogen bonds and the relative occurrence of tautomers are influenced by pi-stacking; electrostatics and natural bond orbital analysis are used to explain these observations. Finally, these conclusions are independent of the precise nature of the multiply hydrogen-bonded systems, including the DNA base pairs.
Original languageEnglish
Pages (from-to)3667-3670
JournalOrganic Letters
Issue number21
Publication statusPublished - 2004


  • density-functional theory
  • ab-initio
  • supramolecular polymers
  • guanine-cytosine
  • base-pairs
  • complexes
  • model
  • systems
  • thymine

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