A 2:1 Co-Crystal of Hydroquinone and 3,5-Bis(2-pyridyl)-1,2,4-triazole

Nieuwenhuyzen, Mark; Keyes, Tia E.; Gallagher, John F.; Vos, Johannes G.

doi:10.1107/s0108270197009670

Cited by 4 publications

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References 3 publications

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“…As illustrated in Scheme , X-ray crystallography reveals that H 2 Q exists within the cocrystal in a well-defined microenvironment. The self-assembly of the HQBpt cocrystal is driven by π−π interactions and extensive three-dimensional H-bonding . There is no direct bonding interaction between molecules that act as linkers in a chain binding HBpt dimers.…”

Section: Resultsmentioning

confidence: 99%

“…Given that the hydroquinones are bound within a solid crystal, D p hys , is assumed to be zero. The intersite separation has been estimated from the X-ray crystal structure . The hydroquinones do not interact directly in the cocrystal but are coupled via H-bridges to the π-stacked HBpt moieties at a through-space distance of approximately 9.4 Å.…”

Section: Resultsmentioning

confidence: 99%

“…Cocrystal of 1,4-Hydroquinone and 3,5-Bis(2-pyridyl)-1,2,4-triazole. The cocrystal was prepared via a technique modified from that described previously . A solution of hydroquinone, (0.1 g, 9 × 10 -4 mol) in ethanol (10 cm 3 ) was added to Hbpt, (0.3 g, 1.4 × 10 -3 mol) in ethanol, 10 cm 3 , and the resulting tan precipitate was recrystallized from ethanol/water, 2:1.…”

Section: Methodsmentioning

confidence: 99%

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Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

et al. 2001

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Solid-state voltammetry, spectroscopy, and microscopy studies have been used to probe the proton and electron conductivity within a self-assembled cocrystal, HQBpt. This crystallographically defined material contains 3,5-bis(pyridin-2-yl)-1,2,4-triazole, HBpt, dimers that are pi-stacked and hydrogen bonded to 1,4-hydroquinone, H(2)Q, in a herringbone arrangement. When deposited onto platinum microelectrodes, the cocrystal exhibits a well-defined voltammetric response corresponding to oxidation of H(2)Q to the quinone, Q, across a wide range of voltammetric time scales, electrolyte compositions, and pH values. Scanning electron microscopy reveals that redox cycling in aqueous perchlorate solutions in which the pH is systematically varied from 1 to 7 triggers electrocrystallization and the extensive formation of rodlike crystals. Fast scan rate voltammetry reveals that the homogeneous charge transport diffusion coefficient, D(app), is independent of the perchlorate concentration for 0.1 < [ClO(4)(-)] < 1.0 M (pH 6.6) at 3.14 +/- 0.11 x 10(-)(9) cm(2) s(-)(1). Moreover, D(app) is independent of the perchloric acid concentration for concentrations greater than approximately 2.0 M, maintaining a value of 4.81 +/- 0.07 x 10(-)(8) cm(2) s(-)(1). The observation that D(app) is independent of the supporting electrolyte suggests that the rate-determining step for homogeneous charge transport is not the availability of charge-compensating counterions or protons, but the dynamics of electron self-exchange between H(2)Q and Q. We have used the Dahms-Ruff formalism to determine electron self-exchange rate constants which are 2.84 +/- 0.22 x 10(9) and 9.69 +/- 0.73 x 10(10) M(-)(1) s(-)(1) for pH values greater than approximately 2.0 and less than -0.3, respectively. Significantly, these values are more than 2 orders of magnitude larger that those found for benzoquinone self-exchange reactions in aqueous solution. These results indicate that hydrogen bonds play an important role in supporting rapid electron transfer. The increase in D(app) between pH 1.0 and -0.3 is associated with protonation of the HBpt moieties, which triggers a reversible change in the material's structure.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

et al. 2001

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“…Especially hydrogenbonding and stacking interactions play important roles in crystal packing, molecular recognition, and the stability of suprastructures although they are weaker than the covalent force [6]. In the case of hydrogen-bond supported supramolecular compounds, the flexibility in proton donation and/or acceptance of the donor and acceptor allows the formation of new compounds with well-designed geometries [7]. The asymmetric unit of the title compound contains one half of 2,5-dichloro-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione (H 2 CA), sitting on an inversion centre and its symmetrygenerated counterparts are linked by hydrogen bonds to the O = P of triphenylphosphineoxide molecules (cf.…”

Section: Discussionmentioning

confidence: 99%

The crystal structure of triphenylphosphineoxide – 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione (2/1), C₄₂H₃₂Cl₂O₆P₂

Belay

Venter

Roodt

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 42 H 32 Cl 2 O 6 P 2 , P1 (no. 2), a = 8.4669(12) Å, b = 9.7245(14) Å, c = 12.2425(17) Å, α = 69.887(6)°, β = 77.758(6)°, γ = 74.915(6)°, CCDC no.: 1527330A part of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on the crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTriphenylphosphineoxide, Ph 3 PO (0.10 g, 0.359 mmol) was dissolved in acetonitrile (5 mL), and treated with 2,5-dichloro-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione, H 2 CA (0.08 g, 0.359 mmol) at room temperature. The resulting mixture was stirred for 6 h, and then the volatile material was removed in vacuo. The resulting reddish was washed with diethyl ether (2 × 10 mL), and dried in vacuo. The product was dissolved in acetonitrile/methanol (4:1) and the solution was left to stand at 255 K for a few days after which orange plate crystals were obtained. IR(ATR): ν PO = 979(vs) and 1118 (m) cm −1 .

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Synthesis, Crystal Structures, and Magnetic Properties of Three New Iron Complexes Derived from 3,5‐Bis(pyridin‐2‐yl)‐1,2,4‐triazole

Chen¹,

Hu²,

Zhou³

et al. 2006

Zeitschrift anorg allge chemie

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Two new iron(III) complexes and one iron(II) complex have been synthesized from the solvothermal reactions of FeCl3·6H2O with 3,5‐bis(pyridin‐2‐yl)‐1,2,4‐triazole (Hbpt) in methanol or acetonitrile. KSCN acted as the reducing agent in the synthesis of iron(II) complex of 3. [FeCl3(Hbpt)(H2O)]·H2O (1) crystallizes in the triclinic space group $P{\bar 1}$ with a = 7.475(1), b = 9.468(2), c = 12.309(2) Å, α = 73.880(2), β = 74.746(2), γ = 81.849(2)°, V = 805.2(2) Å3, Z = 2. [Fe2(bpt)2Cl4] (2): orthorhombic space group Pnnm with a = 9.895(2), b = 10.632(2), c = 13.195(2) Å, V = 1388.1(4) Å3, Z = 2. [Fe2(bpt)2(MeOH)2Cl2] (3): orthorhombic space group Pbca with a = 14.4204(16), b = 9.8737(11), c = 19.792(2) Å, V = 2818.1(5) Å3, Z = 4. 1 features the first structurally characterized metal complex of the neutral Hbpt ligand in which the Hbpt ligand adopts an unprecedented zwitterionic form. 2 shows a neutral dinuclear iron(III) complex and the [Fe2(bpt)2]4+ unit is ideally planar. The two iron(III) ions separated by a distance of 4.408(2) Å are doubly triazolate‐bridged. Each dimeric unit is connected with six other dimeric ones via the bifurcated C‐H···Cl hydrogen bonds, these connections extend the dimeric moieties into a three‐dimensional molecular architecture. 3 is a neutral centrosymmetric dinuclear FeII complex, in which intermolecular moderate O‐H···N hydrogen bonding interactions between the methanol molecules and 4‐position nitrogen atoms of the triazolato groups extend the dinuclear species into a two‐dimensional supramolecular architecture of (4,4) topology. Magnetic studies indicate there exists an antiferromagnetic spin coupling in FeIII2 and FeII2 units via the double triazolate bridges in 2 and 3.

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A 2:1 Co-Crystal of Hydroquinone and 3,5-Bis(2-pyridyl)-1,2,4-triazole

Abstract: The title compound, 2CI2H9N5

Cited by 4 publications

References 3 publications

Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

The crystal structure of triphenylphosphineoxide – 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione (2/1), C₄₂H₃₂Cl₂O₆P₂

Synthesis, Crystal Structures, and Magnetic Properties of Three New Iron Complexes Derived from 3,5‐Bis(pyridin‐2‐yl)‐1,2,4‐triazole

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A 2:1 Co-Crystal of Hydroquinone and 3,5-Bis(2-pyridyl)-1,2,4-triazole

Abstract: The title compound, 2CI2H9N5

Cited by 4 publications

References 3 publications

Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

Electron Self-Exchange in the Solid-State: Cocrystals of Hydroquinone and Bipyridyl Triazole

The crystal structure of triphenylphosphineoxide – 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione (2/1), C42H32Cl2O6P2

Synthesis, Crystal Structures, and Magnetic Properties of Three New Iron Complexes Derived from 3,5‐Bis(pyridin‐2‐yl)‐1,2,4‐triazole

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The crystal structure of triphenylphosphineoxide – 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione (2/1), C₄₂H₃₂Cl₂O₆P₂