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Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems
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dc.contributor.author | Hogan, Simon William Leslie | |
dc.contributor.author | van Mourik, Tanja | |
dc.date.accessioned | 2017-01-16T00:32:05Z | |
dc.date.available | 2017-01-16T00:32:05Z | |
dc.date.issued | 2016-03-30 | |
dc.identifier | 230746103 | |
dc.identifier | e1a2e812-6f59-4a36-b61c-1daaf9b8b5d8 | |
dc.identifier | 84961285683 | |
dc.identifier | 000371489600006 | |
dc.identifier.citation | Hogan , S W L & 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 | en |
dc.identifier.issn | 1096-987X | |
dc.identifier.other | ORCID: /0000-0001-7683-3293/work/57088455 | |
dc.identifier.uri | https://hdl.handle.net/10023/10106 | |
dc.description.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. | |
dc.format.extent | 1384036 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of Computational Chemistry | en |
dc.subject | Halogen bond | en |
dc.subject | Hydrogen bond | en |
dc.subject | Methyluracil | en |
dc.subject | Density functional theory | en |
dc.subject | M06-2X | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Competition between hydrogen and halogen bonding in halogenated 1-methyluracil: water systems | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/jcc.24264 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2017-01-15 |
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