Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine-fluorine noncovalent interactions.

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dc.contributor.author Barceló-Oliver, Miquel
dc.contributor.author Estarellas Martín, Carolina
dc.contributor.author García-Raso, Ángel
dc.contributor.author Terrón Homar, Ángel
dc.contributor.author Frontera Beccaria, Antonio
dc.contributor.author Quiñonero Santiago, David
dc.contributor.author Mata, Ignasi
dc.contributor.author Molins, Elies
dc.contributor.author Deyà Serra, Pere Maria
dc.date.accessioned 2018-10-08T11:14:38Z
dc.identifier.uri http://hdl.handle.net/11201/147988
dc.description.abstract [eng] We have recently communicated the important role of lone pair-p, p-p and hydrophobic interactions in the solid architecture of 5-fluoro-1-hexyluracil and 1-hexyluracil (CrystEngComm, 2010, 12, 362-365). As a matter of fact, the simple substitution of a hydrogen atom by a fluorine atom has an enormous consequence in the solid state structure. It has been demonstrated that this is due to an increase in the p-acidity of the ring. In this article we extend the study to other uracil derivatives, where we have changed the hydrophobicity of the hexyl chain by introducing hydrophilic groups in the substituent, such as hydroxyl or carboxylic groups. The latter compounds, i.e. (N1-(3-hydroxypropyl)- 5-fluorouracil and N1-(4-hydroxycarbonylbutyl)-5-fluorouracil monohydrate present interesting fluorine-fluorine interactions that are very important in determining the crystal packing.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1039/C0CE00048E
dc.relation.ispartof Crystengcomm, 2010, vol. 12, p. 3758-3767
dc.rights (c) Barceló-Oliver, Miquel et al., 2010
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Experimental and theoretical study of uracil derivatives: the crucial role of weak fluorine-fluorine noncovalent interactions.
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-08T11:14:38Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords fluorine-fluorine interactions
dc.subject.keywords X-ray structure
dc.subject.keywords uracil derivatives
dc.subject.keywords Molecular Recognition
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1039/C0CE00048E

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