Structure, hydrogen bond network and proton conductivity of new benzimidazole compounds with dicarboxylic acids

Pogorzelec‐Glaser, Katarzyna; Rachocki, Adam; Ławniczak, Paweł; Pietraszko, A.; Pawlaczyk, Cz.; Hilczer, B.; Pugaczowa‐Michalska, M.

doi:10.1039/c2ce26571k

Cited by 29 publications

(25 citation statements)

References 23 publications

(25 reference statements)

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“…The crystallization was carried out by slow evaporation of the solvent at room temperature (about 25 1C), according to the procedure described in ref. 22. Single crystal plates of 10 mm length, 4 mm width, and 2 mm thick were obtained.…”

Section: Synthesis Proceduresmentioning

confidence: 99%

“…14 The pyrazole molecule, like other nitrogen-containing heterocycles (triazole, imidazole, benzimidazole), crystallizes in layer crystal structures held together by a hydrogen bond network, where protons can easily migrate through the crystal within the layers. [15][16][17][18][19][20][21][22] In the case of proton conductors, several proton diffusion mechanisms such as the Grotthuss process, the translocation mechanism, the vehicle mechanism, proton tunneling, and the solitonic mechanism have been proposed to explain the conducting properties. 23,24 The present study was carried out to provide detailed structural, electrical, and optical properties of this new proton conducting material.…”

Section: Introductionmentioning

confidence: 99%

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Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Widelicka

Pogorzelec‐Glaser

Pietraszko

et al. 2017

Phys. Chem. Chem. Phys.

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The crystal structure of 1H-pyrazol-2-ium hydrogen oxalate has been studied at 100 K. It consists of two-dimensional layers built with one-dimensional chains that contain pyrazolium and oxalate acids bonded by N-HO and O-HO hydrogen bonds. According to the X-ray data and the Quantum Theory of Atoms in Molecules, it was shown that weak and moderate hydrogen bonds are present in the crystal at room temperature. The thermal stability was studied with the DSC, TGA, and DTG methods: three endothermic peaks are observed at 384, 420, and 469 K. Conductivity measurements have been performed in the temperature range from 300 to 433 K. At 383 K the pyrazole-oxalic acid framework loses its rigidity and the crystal undergoes an ordered-disordered phase transition. At this temperature, the value of the activation energy of proton conductivity changes from 1.14 to 2.31 eV. The proton conduction pathways and the transport mechanism have been studied with theoretical methods.

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Section: Synthesis Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Widelicka

Pogorzelec‐Glaser

Pietraszko

et al. 2017

Phys. Chem. Chem. Phys.

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“…Intermolecular interactions involving CH groups are also characteristic for benzimidazole and its derivatives with unsubstituted N atoms . The cohesion forces of these crystals are mainly governed by NH⋅⋅⋅N hydrogen bonds, and in solvates with water, methanol and ethanol the bonds NH⋅⋅⋅OH⋅⋅⋅N exist.…”

Section: Hydrogen Bond Networkmentioning

confidence: 99%

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds

et al. 2017

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X‐ray diffraction structure of two new bis [1‐methyl‐3‐(methoxycarbonylmethyl) benzimidazolium]2+ [CuBr4]2− and [ZnBr4]2− compounds has been determined. Zn‐crystal is monoclinic with perfect Td symmetry of the ZnBr4 tetrahedron, whereas the Cu‐compound is orthorhombic with D2d symmetry of CuBr4 tetrahedron. The difference in these structures is described as due to the static Jahn‐Teller effect. Vibrational spectroscopy (1800–3200 cm−1) identified hydrogen bond network. NIR‐UV‐Vis spectra (5000–50000 cm−1) are dominated by ligand‐to‐metal bands with d‐d transition contribution. EPR results (Q‐band) analyzed in terms of the MO‐theory showed a very strong delocalization of unpaired electron density on ligands accompanied by the Cu(II) 4pz orbital contribution. This effect is partially compensated by charge transfer transitions to the EPR g‐factor.

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“…This problem in dicarboxylic acids salts with heterocyclic molecules was investigated by MacDonald and coworkers . These crystals have layered structure with various architectures of hydrogen‐bonding network system allowing proton migration through the crystal: moderate N─H⋯O between heterocyclic molecules, strong O─H⋯O between dicarboxylic acids molecules, and weak C─H⋯O bonds between the layers …”

Section: Introductionmentioning

confidence: 99%

Spectroscopic investigations of the new anhydrous proton‐conducting compound of pyrazole with oxalate acid

Widelicka

Pogorzelec‐Glaser

Pankiewicz

et al. 2019

J Raman Spectroscopy

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Dicarboxylic acid salts are a good group of compounds in which one can study a variety of supramolecular structures as dimers, catemer chains, and rings and are interesting for crystal engineering of proton conductors for applications in solid‐state hydrogen fuel cells. The optical properties of the new proton‐conducting compound of pyrazole with oxalate acid were investigated using Raman and IR spectroscopy taking into account the formal classification of the fundamental modes. To gain more information on the intermolecular interactions and molecular vibrations, experimental data obtained for 1H‐pyrazol‐2‐ium hydrogen oxalate salt were supported by the quantum‐chemical calculations (density functional theory), Hirshfield surfaces and fingerprint plots analysis, and Bader theory calculations. Topological properties of the planar oxalic acid dimer and oxalic acid pyrazole tetramer have been calculated within the quantum theory of atoms in molecules, and it was shown that dominant types of interactions in the investigated salt are medium strength hydrogen‐bonding interactions.

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Structure, hydrogen bond network and proton conductivity of new benzimidazole compounds with dicarboxylic acids

Cited by 29 publications

References 23 publications

Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds

Spectroscopic investigations of the new anhydrous proton‐conducting compound of pyrazole with oxalate acid

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Structure, hydrogen bond network and proton conductivity of new benzimidazole compounds with dicarboxylic acids

Cited by 29 publications

References 23 publications

Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]2+ [CuBr4]2− and [ZnBr4]2− Compounds

Spectroscopic investigations of the new anhydrous proton‐conducting compound of pyrazole with oxalate acid

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Product

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Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds