Experimental and theoretical study of N1-hexylcytosine and N1-hexylcytosinium nitrate: the crucial role of hydrophobic and anion¿pi interactions

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dc.contributor.author Barceló-Oliver, Miquel
dc.contributor.author Bauzá Riera, Antonio
dc.contributor.author Baquero, Beatriz A.
dc.contributor.author García-Raso, Ángel
dc.contributor.author Terrón Homar, Ángel
dc.contributor.author Molins, Elies
dc.contributor.author Frontera Beccaria, Antonio
dc.date.accessioned 2018-09-25T07:29:17Z
dc.identifier.uri http://hdl.handle.net/11201/147631
dc.description.abstract [eng] We report the synthesis and X-ray characterization of N1-hexylcytosine (1) and N1-hexylcytosinium nitrate (2). N1-hexylcytosine (1) does not follow the same behaviour previously described for N1-hexylthymine and N1-hexyluracil in the solid state. This different behavior has been analyzed by means of density functional theory (DFT) calculations including the latest available correction for dispersion (D3). In addition hydrophobic and anion<br>p noncovalent interactions play a key role in stabilizing the 3D architectures of the compounds, which have been energetically studied using theoretical calculations and compared with similar structures retrieved from the Cambridge Structural Database (CSD). The anion<br> pi<br>anion binding mode observed for nitrate in compound 2 is also observed in several crystal structures involving cytosine ring coordinated to transition metals.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1016/j.tetlet.2013.07.099
dc.relation.ispartof Tetrahedron Letters, 2013, vol. 54, p. 5355-5360
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Experimental and theoretical study of N1-hexylcytosine and N1-hexylcytosinium nitrate: the crucial role of hydrophobic and anion¿pi interactions
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-09-25T07:29:17Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords cytosine
dc.subject.keywords anion-pi interaction
dc.subject.keywords DFT calculations
dc.subject.keywords hydrophobic interactions
dc.subject.keywords nitrate
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1016/j.tetlet.2013.07.099


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