Homodromic hydrogen bonds in low-energy conformations of single molecule cyclodextrins

  • Alfred Karpfen
  • Elisabeth Liedl
  • Walter Snor
  • Petra Weiss-Greiler
  • Helmut Viernstein
  • Peter WolschannEmail author
Original Article


Low-energy conformations of β-cyclodextrin under anhydrous conditions in the gas phase were investigated by DFT calculations. In these conformations, two homodromic hydrogen bond rings are formed with very short hydrogen bonds at the narrow side of the cyclodextrin ring and a second one at the wider side. These hypothetical conformations are not comparable to those conformations, which have been studied experimentally, forming inclusion complexes with small and medium-sized guest molecules, but their energy is significantly lower than the open conformations (ΔE = 10 kcal/mol).


Cyclodextrin ab initio Density functional calculations Homodromic hydrogen bonds 



This investigation was supported by the Hochschuljubiläumsstiftung der Stadt Wien (Project P H-778/2005). Technical assistance of Ms. Martina Ziehengraser is gratefully acknowledged.


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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Alfred Karpfen
    • 1
  • Elisabeth Liedl
    • 1
  • Walter Snor
    • 1
  • Petra Weiss-Greiler
    • 1
  • Helmut Viernstein
    • 2
  • Peter Wolschann
    • 1
    Email author
  1. 1.Institute of Theoretical ChemistryUniversity of ViennaWienAustria
  2. 2.Department of Pharmaceutical Technology and BiopharmaceuticsUniversity of ViennaWienAustria

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