Metal–nucleobase interaction: dibromobis(cytosine)cadmium(II)

Muthiah, Packianathan Thomas; Robert, Jebamony Justin; Raj, S. Baskar; Bocelli, Gabriele; Olla, R.

doi:10.1107/s1600536801018360

Cited by 14 publications

(15 citation statements)

References 14 publications

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“…Historically, the great importance of the hydrogen bonding in the formation of many molecular systems is widely known among theoreticians and experimentalists [1][2][3][4][5]. In some specific cases, the hydrogen bonding is considered the main focus in studies about intermediaries in organic reaction mechanisms, such as electrophilic addition [6].…”

Section: Introductionmentioning

confidence: 99%

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

2008

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In this theoretical work, the characterization of multiple proton donors in three isomers of BeH 2 ÁÁÁ2HCl trimolecular dihydrogen-bonded complex was developed through the analysis of structural parameters, electronic criteria, and analysis of vibrational harmonic spectrum, where all these data were obtained from the B3LYP/6-311++G(3d,3p) calculations. As dihydrogen bonds are formed by the interaction between two hydrogen atoms, proton donors and hydride hydrogen, the isomers of BeH 2 ÁÁÁ2HCl trimolecular dihydrogen-bonded complexes are stabilized by two, three, and four centers of proton donors. By analyzing the charge density integrations calculated by the theory of Atoms in Molecules, these multiple centers of proton donors were identified by quantification of the intermolecular electronic density, Laplacian operators, and charge transfers.

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Section: Introductionmentioning

confidence: 99%

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

2008

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“…The amino group of the OMP ligand and the coordinated carboxylate O atom of the 2-TPC ligand form an interligand N-HÁ Á ÁO hydrogen bond (Table 2), generating an S(6) ring motif. This type of interligand hydrogen bond is characteristic of many metal complexes of aminopyrimidine/aminopurines (Muthiah et al, 1983(Muthiah et al, , 2001Karthikeyan et al, 2010). The structure has a combination of O-HÁ Á ÁO and O-HÁ Á ÁCl interactions between the uncoordinated water molecule and the coordinated water molecule, research papers The asymmetric unit of compound (I), showing the atom-numbering scheme.…”

Section: Resultsmentioning

confidence: 97%

Supramolecular architectures in Co^IIand Cu^IIcomplexes with thiophene-2-carboxylate and 2-amino-4,6-dimethoxypyrimidine ligands

2016

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The coordination chemistry of mixed-ligand complexes continues to be an active area of research since these compounds have a wide range of applications. Many coordination polymers and metal-organic framworks are emerging as novel functional materials. Aminopyrimidine and its derivatives are flexible ligands with versatile binding and coordination modes which have been proven to be useful in the construction of organic-inorganic hybrid materials and coordination polymers. Thiophenecarboxylic acid, its derivatives and their complexes exhibit pharmacological properties. Cobalt(II) and copper(II) complexes of thiophenecarboxylate have many biological applications, for example, as antifungal and antitumor agents. Two new cobalt(II) and copper(II) complexes incorporating thiophene-2-carboxylate (2-TPC) and 2-amino-4,6-dimethoxypyrimidine (OMP) ligands have been synthesized and characterized by X-ray diffraction studies, namely (2-amino-4,6-dimethoxypyrimidine-κN)aquachlorido(thiophene-2-carboxylato-κO)cobalt(II) monohydrate, [Co(C5H3O2S)Cl(C6H9N3O2)(H2O)]·H2O, (I), and catena-poly[copper(II)-tetrakis(μ-thiophene-2-carboxylato-κ(2)O:O')-copper(II)-(μ-2-amino-4,6-dimethoxypyrimidine-κ(2)N(1):N(3))], [Cu2(C5H3O2S)4(C6H9N3O2)]n, (II). In (I), the Co(II) ion has a distorted tetrahedral coordination environment involving one O atom from a monodentate 2-TPC ligand, one N atom from an OMP ligand, one chloride ligand and one O atom of a water molecule. An additional water molecule is present in the asymmetric unit. The amino group of the coordinated OMP molecule and the coordinated carboxylate O atom of the 2-TPC ligand form an interligand N-H...O hydrogen bond, generating an S(6) ring motif. The pyrimidine molecules also form a base pair [R2(2)(8) motif] via a pair of N-H...N hydrogen bonds. These interactions, together with O-H...O and O-H...Cl hydrogen bonds and π-π stacking interactions, generate a three-dimensional supramolecular architecture. The one-dimensional coordination polymer (II) contains the classical paddle-wheel [Cu2(CH3COO)4(H2O)2] unit, where each carboxylate group of four 2-TPC ligands bridges two square-pyramidally coordinated Cu(II) ions and the apically coordinated OMP ligands bridge the dinuclear copper units. Each dinuclear copper unit has a crystallographic inversion centre, whereas the bridging OMP ligand has crystallographic twofold symmetry. The one-dimensional polymeric chains self-assemble via N-H...O, π-π and C-H...π interactions, generating a three-dimensional supramolecular architecture.

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“…In addition, two iodide ions are coordinated to Cd1 to complete a distorted tetrahedral environment. The structure is isotypic with [CdBr 2 (C 4 H 5 N 3 O) 2 ] (Muthiah et al, 2001) (Fig. 1).…”

Section: Structure Description Of [Cdi 2 (Cy) 2 ] (I)mentioning

confidence: 99%

“…The interplay of metal coordination and base pairing in nuleobases has become an important area of study. Supramolecular hydrogen-bonding patterns of nucleobase metal complexes have been reported in the literature ISSN 2053ISSN -2296 # 2018 International Union of Crystallography (Thomas-Gipson et al, 2017;Mohapatra et al, 2017;Marino et al, 2016;Lippert et al, 2016;Karthikeyan et al, 2010;Stanley et al, 2006;Muthiah et al, 2001). The synergy between these interactions in nucleobases has led to the development and construction of novel DNA materials in various fields (Amo-Ochoa & Zamora, 2014).…”

Section: Introductionmentioning

confidence: 97%

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

2018

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Three new metal(II)-cytosine (Cy)/5-fluorocytosine (5FC) complexes, namely bis(4-amino-1,2-dihydropyrimidin-2-one-κN)diiodidocadmium(II) or bis(cytosine)diiodidocadmium(II), [CdI(CHNO)], (I), bis(4-amino-1,2-dihydropyrimidin-2-one-κN)bis(nitrato-κO,O')cadmium(II) or bis(cytosine)bis(nitrato)cadmium(II), [Cd(NO)(CHNO)], (II), and (6-amino-5-fluoro-1,2-dihydropyrimidin-2-one-κN)aquadibromidozinc(II)-6-amino-5-fluoro-1,2-dihydropyrimidin-2-one (1/1) or (6-amino-5-fluorocytosine)aquadibromidozinc(II)-4-amino-5-fluorocytosine (1/1), [ZnBr(CHFNO)(HO)]·CHFNO, (III), have been synthesized and characterized by single-crystal X-ray diffraction. In complex (I), the Cd ion is coordinated to two iodide ions and the endocyclic N atoms of the two cytosine molecules, leading to a distorted tetrahedral geometry. The structure is isotypic with [CdBr(CHNO)] [Muthiah et al. (2001). Acta Cryst. E57, m558-m560]. In compound (II), each of the two cytosine molecules coordinates to the Cd ion in a bidentate chelating mode via the endocyclic N atom and the O atom. Each of the two nitrate ions also coordinates in a bidentate chelating mode, forming a bicapped distorted octahedral geometry around cadmium. The typical interligand N-H...O hydrogen bond involving two cytosine molecules is also present. In compound (III), one zinc-coordinated 5FC ligand is cocrystallized with another uncoordinated 5FC molecule. The Zn atom coordinates to the N(1) atom (systematic numbering) of 5FC, displacing the proton to the N(3) position. This N(3)-H tautomer of 5FC mimics N(3)-protonated cytosine in forming a base pair (via three hydrogen bonds) with 5FC in the lattice, generating two fused R(8) motifs. The distorted tetrahedral geometry around zinc is completed by two bromide ions and a water molecule. The coordinated and nonccordinated 5FCs are stacked over one another along the a-axis direction, forming the rungs of a ladder motif, whereas Zn-Br bonds and N-H...Br hydrogen bonds form the rails of the ladder. The coordinated water molecules bridge the two types of 5FC molecules via O-H...O hydrogen bonds. The cytosine molecules are coordinated directly to the metal ion in each of the complexes and are hydrogen bonded to the bromide, iodide or nitrate ions. In compound (III), the uncoordinated 5FC molecule pairs with the coordinated 5FC ligand through three hydrogen bonds. The crystal structures are further stabilized by N-H...O, N-H...N, O-H...O, N-H...I and N-H...Br hydrogen bonds, and stacking interactions.

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Metal–nucleobase interaction: dibromobis(cytosine)cadmium(II)

Cited by 14 publications

References 14 publications

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

Supramolecular architectures in Co^IIand Cu^IIcomplexes with thiophene-2-carboxylate and 2-amino-4,6-dimethoxypyrimidine ligands

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

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Metal–nucleobase interaction: dibromobis(cytosine)cadmium(II)

Cited by 14 publications

References 14 publications

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

Multiple proton donors on BeH2···2HCl trimolecular dihydrogen-bonded complex: some theoretical insights

Supramolecular architectures in CoIIand CuIIcomplexes with thiophene-2-carboxylate and 2-amino-4,6-dimethoxypyrimidine ligands

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

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Supramolecular architectures in Co^IIand Cu^IIcomplexes with thiophene-2-carboxylate and 2-amino-4,6-dimethoxypyrimidine ligands