Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems

Simon William Leslie Hogan, Tanja van Mourik

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The competition between hydrogen- and halogen-bonding interactions in complexes of 5-halogenated 1-methyluracil (XmU; X = F, Cl, Br, I or At) with one or two water molecules in the binding region between C5-X and C4=O4 is investigated with M06-2X/6-31+G(d). In the singly-hydrated systems, the water molecule forms a hydrogen bond with C4=O4 for all halogens, whereas structures with a halogen bond between the water oxygen and C5-X exist only for X = Br, I and At. Structures with two waters forming a bridge between C4=O and C5-X (through hydrogen- and halogen-bonding interactions) exist for all halogens except F. The absence of a halogen-bonded structure in singly-hydrated ClmU is therefore attributed to the competing hydrogen-bonding interaction with C4=O4. The halogen-bond angle in the doubly-hydrated structures (150-160°) is far from the expected linearity of halogen bonds, indicating that significantly non-linear halogen bonds may exist in complex environments with competing interactions.
Original languageEnglish
Pages (from-to)763-770
JournalJournal of Computational Chemistry
Issue number8
Early online date15 Jan 2016
Publication statusPublished - 30 Mar 2016


  • Halogen bond
  • Hydrogen bond
  • Methyluracil
  • Density functional theory
  • M06-2X


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