title: Experimental and theoretical studies on the coordination chemistry of the N1-hexyl substituted pyrimidines (uracil, 5-fluorouracil and cytosine).
abstract: N(1)-Hexyl substituted pyrimidines were shown to present solubility properties closer to the real bases than the commonly used methyl and ethyl derivatives, yielding bi-layered structures in the solid state. The study of their coordination capabilities, mainly with Ag(I) and Hg(II), is presented in order to prove their reactivity. A series of coordination complexes, namely, [Hg(N(1)-hexyl-5-fluorouracilate)2]4·6H2O (1), (Ag(+))·[Ag(N(1)-hexyl-5-fluorouracilate)2](-) (2), [Ag(NO3)(N(1)-hexyluracil-κO(4))4] (3), [ZnBr2(N(1)-hexylcytosine)2] (4), [CdBr2(N(1)-hexylcytosine)2] (5), [HgBr2(N(1)-hexylcytosine)2] (6) and [CoBr2(N(1)-hexylcytosine)2] (7), have been synthesized in good yields and X-ray characterized. The presence of the hexyl chains and the fluorine atoms causes the formation of interesting 3D architectures in the solid state. Their structures have been further characterized by infrared spectra (IR) and elemental analyses. In addition, DFT-D3 calculations are used to study interesting noncovalent interactions observed in the solid state, like fluorine-fluorine, fluorine-π and hydrophobic interactions.
authors.affiliation: Departament de Química, Universitat de les Illes Balears, Carretera Valldemossa km 7.5, E-07122 Palma de Mallorca, Illes Balears, Spain. miquel.barcelo@uib.es
authors.forename: Miquel
authors.initials: M
authors.lastname: Barceló-Oliver
authors.forename: Beatriz Adriana
authors.initials: BA
authors.lastname: Baquero
authors.forename: Antonio
authors.initials: A
authors.lastname: Bauzá
authors.forename: Angel
authors.initials: A
authors.lastname: García-Raso
authors.forename: Roberto
authors.initials: R
authors.lastname: Vich
authors.forename: Ignasi
authors.initials: I
authors.lastname: Mata
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.forename: Angel
authors.initials: A
authors.lastname: Terrón
authors.forename: Antonio
authors.initials: A
authors.lastname: Frontera
mesh_terms: D056831:Coordination Complexes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003596:Cytosine / Q000737:chemistry*; D008628:Mercury / Q000737:chemistry*; D008958:Models, Molecular; D011789:Quantum Theory; D012834:Silver / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*
chemical_list: D056831:Coordination Complexes; D012834:Silver; D014498:Uracil; D003596:Cytosine; D008628:Mercury