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

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Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems. / Hogan, Simon William Leslie; van Mourik, Tanja.

In: Journal of Computational Chemistry, Vol. 37, No. 8, 30.03.2016, p. 763-770.

Research output: Contribution to journalArticlepeer-review

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Hogan, SWL & van Mourik, T 2016, 'Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems', Journal of Computational Chemistry, vol. 37, no. 8, pp. 763-770. https://doi.org/10.1002/jcc.24264

APA

Hogan, S. W. L., & van Mourik, T. (2016). Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems. Journal of Computational Chemistry, 37(8), 763-770. https://doi.org/10.1002/jcc.24264

Vancouver

Hogan SWL, van Mourik T. Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems. Journal of Computational Chemistry. 2016 Mar 30;37(8):763-770. https://doi.org/10.1002/jcc.24264

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Hogan, Simon William Leslie ; van Mourik, Tanja. / Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems. In: Journal of Computational Chemistry. 2016 ; Vol. 37, No. 8. pp. 763-770.

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@article{e1a2e8126f594a36b61c1daaf9b8b5d8,
title = "Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems",
abstract = "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.",
keywords = "Halogen bond, Hydrogen bond, Methyluracil, Density functional theory, M06-2X",
author = "Hogan, {Simon William Leslie} and {van Mourik}, Tanja",
year = "2016",
month = mar,
day = "30",
doi = "10.1002/jcc.24264",
language = "English",
volume = "37",
pages = "763--770",
journal = "Journal of Computational Chemistry",
issn = "0192-8651",
publisher = "John Wiley & Sons, Ltd.",
number = "8",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems

AU - Hogan, Simon William Leslie

AU - van Mourik, Tanja

PY - 2016/3/30

Y1 - 2016/3/30

N2 - 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.

AB - 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.

KW - Halogen bond

KW - Hydrogen bond

KW - Methyluracil

KW - Density functional theory

KW - M06-2X

U2 - 10.1002/jcc.24264

DO - 10.1002/jcc.24264

M3 - Article

VL - 37

SP - 763

EP - 770

JO - Journal of Computational Chemistry

JF - Journal of Computational Chemistry

SN - 0192-8651

IS - 8

ER -

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