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dc.contributor.authorThornton, Nicholas J.
dc.contributor.authorvan Mourik, Tanja
dc.identifier.citationThornton , N J & van Mourik , T 2020 , ' Halogen-bonded guanine base pairs, quartets and ribbons ' , International Journal of Molecular Sciences , vol. 21 , no. 18 , 6571 .
dc.identifier.otherPURE: 270007069
dc.identifier.otherPURE UUID: eec75ed1-23a6-4967-99f5-aae92ae595f4
dc.identifier.otherORCID: /0000-0001-7683-3293/work/80257719
dc.identifier.otherScopus: 85090622322
dc.identifier.otherWOS: 000580030300001
dc.description.abstractHalogen bonding is studied in different structures consisting of halogenated guanine DNA bases, including the Hoogsteen guanine–guanine base pair, two different types of guanine ribbons (R-I and R-II) consisting of two or three monomers, and guanine quartets. In the halogenated base pairs (except the Cl-base pair, which has a very non-planar structure with no halogen bonds) and R-I ribbons (except the At trimer), the potential N-X•••O interaction is sacrificed to optimise the N-X•••N halogen bond. In the At trimer, the astatines originally bonded to N1 in the halogen bond donating guanines have moved to the adjacent O6 atom, enabling O-At•••N, N-At•••O, and N-At•••At halogen bonds. The brominated and chlorinated R-II trimers contain two N-X•••N and two N-X•••O halogen bonds, whereas in the iodinated and astatinated trimers, one of the N-X•••N halogen bonds is lost. The corresponding R-II dimers keep the same halogen bond patterns. The G-quartets display a rich diversity of symmetries and halogen bond patterns, including N-X•••N, N-X•••O, N-X•••X, O-X•••X, and O-X•••O halogen bonds (the latter two facilitated by the transfer of halogens from N1 to O6). In general, halogenation decreases the stability of the structures. However, the stability increases with the increasing atomic number of the halogen, and the At-doped R-I trimer and the three most stable At-doped quartets are more stable than their hydrogenated counterparts. Significant deviations from linearity are found for some of the halogen bonds (with halogen bond angles around 150°).
dc.relation.ispartofInternational Journal of Molecular Sciencesen
dc.rightsCopyright © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open accessarticle distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (
dc.subjectGuanine-guanine base pairen
dc.subjectGuanine ribbonsen
dc.subjectGuanine quarteten
dc.subjectDensity functional theoryen
dc.subjectDispersion correctionen
dc.subjectQD Chemistryen
dc.titleHalogen-bonded guanine base pairs, quartets and ribbonsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.Centre for Research into Equality, Diversity & Inclusionen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.description.statusPeer revieweden

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