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Issue 21, 2013
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Experimental and theoretical studies on the coordination chemistry of the N1-hexyl substituted pyrimidines (uracil, 5-fluorouracil and cytosine)

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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(N1-hexyl-5-fluorouracilate)2]4·6H2O (1), (Ag+)·[Ag(N1-hexyl-5-fluorouracilate)2] (2), [Ag(NO3)(N1-hexyluracil-κO4)4] (3), [ZnBr2(N1-hexylcytosine)2] (4), [CdBr2(N1-hexylcytosine)2] (5), [HgBr2(N1-hexylcytosine)2] (6) and [CoBr2(N1-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.

Graphical abstract: Experimental and theoretical studies on the coordination chemistry of the N1-hexyl substituted pyrimidines (uracil, 5-fluorouracil and cytosine)

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Publication details

The article was received on 05 Dec 2012, accepted on 06 Mar 2013 and first published on 06 Mar 2013


Article type: Paper
DOI: 10.1039/C3DT32922D
Citation: Dalton Trans., 2013,42, 7631-7642
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    Experimental and theoretical studies on the coordination chemistry of the N1-hexyl substituted pyrimidines (uracil, 5-fluorouracil and cytosine)

    M. Barceló-Oliver, B. A. Baquero, A. Bauzá, Á. García-Raso, R. Vich, I. Mata, E. Molins, À. Terrón and A. Frontera, Dalton Trans., 2013, 42, 7631
    DOI: 10.1039/C3DT32922D

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