Crystal engineering with coordination compounds of NiII, CoII, and CrIII bearing dipicolinic acid driven by the nature of the noncovalent interactions

Mirzaei, Masoud; Eshtiagh‐Hosseini, Hossein; Karrabi, Zahra; Molčanov, Krešimir; Eydizadeh, Ehsan; Mague, Joel T.; Bauzá, Antonio; Frontera, Antonio

doi:10.1039/c4ce00325j

Cited by 86 publications

(31 citation statements)

References 60 publications

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“…Logically, protonated 9-aminoacridine molecules are arranged in an antiparallel stacking mode [40]. The geometry, bond distances and angles of 3 are comparable with similar compounds reported in the literature [41][42][43].…”

Section: Crystal Structures Of 3 Andsupporting

confidence: 62%

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

2015

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Four new supramolecular coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide formulated as (Htata) (Hpydco)ÁH 2 O (1), (Htata) 2 (pydco)Á2H 2 O (2), (H9a-acr) 2 [Zn(pydco) 2 (H 2 O) 2 ]Á4H 2 O (3), and (H9a-acr) 2 [Co(pydco) 2 (H 2 O) 2 ]Á4H 2 O (4) (where H 2 pydco = pyridine-2,6-dicarboxylic acid N-oxide, tata = 2,4,6-triamino-1,3,5-triazine (melamine) and 9a-acr = 9-aminoacridine) have been synthesized by proton transfer from H 2 pydco as ligand and to tata and 9a-acr. The structures of 1-4 were characterized by elemental analysis, infrared spectroscopy, and single crystal X-ray diffraction methods. Compounds 1 and 2 are salts of proton-transferred H 2 pydco and melamine with two separate formulas. There is a difference between the anionic fragment in 1 and 2, the anionic part of 1 retains one acid proton (Hpydco -) which is involved in a strong, intramolecular hydrogen bonding with the oxygen attached to nitrogen, while the acid units in 2 are fully deprotonated (pydco 2-). The linear chains of melaminium cations with an anionic motif and water molecules lead to 2-D zipper layers in 1 and 2-D zigzag layers in 2. These layers are held together via an extensive network of hydrogen bonds, p ? -p 1 stacking, N ? -H_p ? , and lp_p ? interactions to extend the structures into the 3-D supramolecular framework. Single-crystal studies revealed that 3 and 4 are isostructural with distorted octahedral geometry about the metal consisting of two pydco 2-ligands acting in bidentate fashion and two transdisposed water molecules. They also adopt alternating cationic and anionic layers with 9-aminoacridinium cations and transition metal complex anions which are linked to each other by a variety of noncovalent interactions such as ion pairing, hydrogen bonding and p-p stacking.

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Section: Crystal Structures Of 3 Andsupporting

confidence: 62%

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

2015

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“…Each dicationic moiety is hydrogen‐bonded to the anionic trinuclear Cd complex via two strong hydrogen bonds (red dashed lines). Several previous works have been devoted to the analysis of the so‐called π + –π + interactions, which are similar in nature to the conventional π‐stacking interaction and the anionic counterions are needed to thermodynamically stabilize the assembly.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Pons

Ibáñez

Buades

et al. 2019

Applied Organom Chemis

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We report the synthesis and X-ray characterization of the N 6 -benzyl-N 6methyladenine ligand (L) and three metal complexes, namely [Zn(HL) Cl 3 ]·H 2 O (1), [Cd(HL) 2 Cl 4 ] (2) and [H 2 L] 2 [Cd 3 (μ-L) 2 (μ-Cl) 4 Cl 6 ]·3H 2 O (3). Complex 1 consists of the 7H-adenine tautomer protonated at N3 and coordinated to a tetrahedral Zn(II) metal centre through N9. The octahedral Cd(II) in complex 2 is N 9 -coordinated to two N 6 -benzyl-N 6 -methyladeninium ligands (7H-tautomer protonated at N3) that occupy apical positions and four chlorido ligands form the basal plane. Compound 3 corresponds to a trinuclear Cd(II) complex, where the central Cd atom is six-coordinated to two bridging μ-L and four bridging μ-Cl ligands. The other two Cd atoms are six-coordinated to three terminal chlorido ligands, to two bridging μ-Cl ligands and to the bridging μ-L through N3. Essentially, the coordination patterns, degree of protonation and tautomeric forms of the nucleobase dominate the solid-state architectures of 1-3. Additionally, the hydrogen-bonding interactions produced by the endocyclic N atoms and NH groups stabilize high-dimensional-order supramolecular assemblies. Moreover, energetically strong anion-π and lone pair (lp)-π interactions are important in constructing the final solid-state architectures in 1-3. We have studied the non-covalent interactions energetically using density functional theory calculations and rationalized the interactions using molecular electrostatic potential surfaces and Bader's theory of atoms in molecules. We have particularly analysed cooperative lp-π and anion-π interactions in 1 and π + -π + interactions in 3.

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“…Considerable effort has been devoted to the syntheses and characterizations of metal-organic frameworks (MOFs) composed of transition metal ions and organic ligands because of their unmatched structural versatilities and potential applications such as gas storage, separation, absorption chemistry, luminescence, catalysis, sensors and magnetism [1][2][3][4][5][6][7][8][9][10][11]. Binuclear and polynuclear complexes containing monoatomic and multidentate bridging ligands are of considerable interest from the standpoint of inorganic and bioinorganic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure, solution and DFT studies of a pyrazine-bridged binuclear Cu(II) complex: On the importance of noncovalent interactions in the formation of crystalline network

Mirzaei

Eshtiagh‐Hosseini

Karrabi

et al. 2015

Journal of Molecular Structure

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Crystal engineering with coordination compounds of NiII, CoII, and CrIII bearing dipicolinic acid driven by the nature of the noncovalent interactions

Cited by 86 publications

References 60 publications

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Synthesis, structure, solution and DFT studies of a pyrazine-bridged binuclear Cu(II) complex: On the importance of noncovalent interactions in the formation of crystalline network

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Crystal engineering with coordination compounds of NiII, CoII, and CrIII bearing dipicolinic acid driven by the nature of the noncovalent interactions

Cited by 86 publications

References 60 publications

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide

Synthesis, X‐ray characterization and density functional theory studies of N6‐benzyl‐N6‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions

Synthesis, structure, solution and DFT studies of a pyrazine-bridged binuclear Cu(II) complex: On the importance of noncovalent interactions in the formation of crystalline network

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Synthesis, X‐ray characterization and density functional theory studies of N⁶‐benzyl‐N⁶‐methyladenine–M(II) complexes (M = Zn, Cd): The prominent role of π–π, C–H···π and anion–π interactions