Supramolecular hydrogen-bonding network in 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate crystal

Perpétuo, Genivaldo Júlio; Gonçalves, Rafael Silva Ribeiro; Janczak, Jan

doi:10.1016/j.molstruc.2015.04.037

Cited by 11 publications

(7 citation statements)

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“…Both arms of the 1-(diaminomethylene)thiouron-1-ium are rotated around C-N bond involving the central N1 atom. Compared to neutral 1-(diaminomethylene)thiourea, where the observed dihedral angle is 22.2(1)° [2], the protonation on N1 reduces the steric effect of lone pair of electrons and the dihedral angle decreases to 6.0(3)°. The conformation of the anion compares to bis(dihydronium) naphthalene-1,5-disulfonate [3], with one oxygen (O3) laying on the ring.…”

Section: Commentsmentioning

confidence: 85%

“…Commercially available 2-imino-4-thiobiuret, which is in the fact the tautomeric form (schemme 1), 1-(diaminomethylene)thiourea [2] and the 1,5-naphthalenedisulfonic acid tetrahydrate were added to hot water in a molar proportion of 2:1. After several days, transparent colourless crystals were formed.…”

Section: Methodsmentioning

confidence: 99%

“…The C=S stretching is observed on 730 cm -1 . Skeletal deformations C-N-C, N-C-N and SO 3 − asymmetric deformation are observed on 564 cm -1 [2,4].…”

Section: Figure 3: One Layer Viewed Along C Axis With N-h•••o and N-hmentioning

confidence: 99%

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Supramolecular hydrogen-bonding network in bis[1-(diaminomethylene)thiouron-1-ium] naphthalene-1,5-disulfonate

Felix¹,

Janczak²,

Perpétuo³

2017

Blucher Material Science Proceedings

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Intermolecular interactions are important for the understanding of molecular selforganization of new solids with desired physical and chemical properties [1]. In this work crystals of bis[(1-diaminomethylene)thiouron-1-ium] naphthalene-1,5-disulfonate were grown using solution growth technique. A single-crystal sample was characterized by X-ray diffraction and FTIR spectroscopy. The compound crystallizes in centrosymmetric group C2/c of the monoclinic system. The conformations of the cation bis[1-(diaminomethylene)thiouron-1-ium] and the anion naphthalene 1,5-disulfonate are shown in figure 1. Experimental:Commercially available 2-imino-4-thiobiuret, which is in the fact the tautomeric form (schemme 1), 1-(diaminomethylene)thiourea [2] and the 1,5-naphthalenedisulfonic acid tetrahydrate were added to hot water in a molar proportion of 2:1. After several days, transparent colourless crystals were formed. The crystals have been separated by filtration and dried in air. Analysis: Calculated for C14H20N8O6S4: C, 32.05; N, 21.26; O, 18.30; S, 24.45 and H, 3.84%. Found: C, 31.88; N, 21.32; O, 18.63; S, 24.39 and H, 3.78%. A colourless 0.05 mm x 0.02 mm x 0.05 mm sample was mounted on a Gemini Oxford CCD Diffractometer provided with a liquid nitrogen low-temperature device. IR data measured with an ABB Bomen MB 3000 FTIR spectrometer using KBr pellets. Schemme 1: Tautomeric equilibrium forms of 1-(diaminomethylene)thiourea and 2-imino-4-thiobiuret

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Section: Commentsmentioning

confidence: 85%

Section: Methodsmentioning

confidence: 99%

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Supramolecular hydrogen-bonding network in bis[1-(diaminomethylene)thiouron-1-ium] naphthalene-1,5-disulfonate

Felix¹,

Janczak²,

Perpétuo³

2017

Blucher Material Science Proceedings

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“…However, in the case of form II, it could be observed that the band in the region between 1150 cm −1 to 1240 cm −1 , corresponding to the asymmetric stretches of the sulfonate group, is not sharp, and instead exhibits little splitting with line broadening (Figure 4). This could be attributed to loss of local symmetry around the SO − 3 group in the form II, [33][34][35][36] when compared to form I, due to the enriched hydrogen bonding interactions of the sulfonate group of the form II, 6b as seen in its supramolecular structure. The symmetric stretching vibrations of the group, for both the forms occur in the region from 1025 cm −1 to 1090 cm −1 .…”

Section: Ft-ir Analytical and Pxrd Studiesmentioning

confidence: 99%

“…The broad peaks between 2950 cm −1 to 3550 cm −1 could originate from the combined presences of the hydrogen bonded N-H and O-H stretching vibrations of the imidzolium and water molecules of the forms. [33][34][35][36][37] The sharp peaks around 500 cm −1 to 600 cm −1 could very well be attributed to the presence of lattice water molecules. 37 Similarly, the TGA analysis as well, distinguishes the lattice water molecules of both the forms in their respective thermograms, through their percentage weight loss.…”

Section: Ft-ir Analytical and Pxrd Studiesmentioning

confidence: 99%

Facile crystallization of 2-phenyl benzimidazole-5-sulfonic acid: Characterization of lattice water dependent zwitterionic supramolecular forms, with modulation in proton conductivities

2019

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A facile aqueous medium crystallization strategy has been found for this water insoluble title compound. Two crystalline forms, differing in the number of lattice water molecules (mono hydrated; form I & di-hydrated; form II), have been obtained, depending on the duration of crystallization. X-ray structural studies reveal that the compound crystallizes in the zwitterionic state in both the forms, due to the protonation of one imidazole nitrogen by-SO 3 H group, are engaged in hydrogen bonded interactions, involving lattice water molecule(s), and thus the supramolecular arrangements of the forms are influenced by lattice waters. Additional water molecules in the form II make it more hydrophilic, as confirmed using contact angle measurements. Procedures were optimized for better crystalline yields, and the bulk purity were ascertained by TGA, elemental and PXRD analysis. AC impedance measurements prove that both the crystalline forms are indeed proton conducting electrolytes, with magnitudes of 1 × 10 −5 S cm −1 and 5 × 10 −5 S cm −1 for form I & II, respectively under humidified conditions at 25 • C. Proton conducting performance of II has been found to be greater than I and could be correlated with its higher hydrophilicity and enriched hydrogen bonds for Grotthuss mechanism.

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Regulating the Interfacial Charge Density by Constructing a Novel Zn Anode‐Electrolyte Interface for Highly Reversible Zn Anode

Zhan,

Guo,

et al. 2023

Chemistry A European J

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Aqueous zinc‐ion batteries (AZIBs) have attracted considerable attention. However, due to the uneven distribution of charge density at Zn anode|electrolyte interface, severe dendrites and corrosion are generated during cycling. In this work, a facile and scalable strategy to address the above‐mentioned issues has been proposed through regulating the charge density at Zn anode|electrolyte interface. As a proof of concept, amidinothiourea (ATU) with abundant lone‐pair electrons is employed as an interfacial charge modifier for Zn anode|electrolyte interface. The uniform and increased interfacial charge distribution on Zn anode|electrolyte interface has been obtained. Moreover, the unique Zn‐bond constructed between N atoms and Zn2+ as well as the hydrogen bonds are formed among ATU and Ac‐ anion/active H2O, which promote the migration and desolvation behavior of Zn2+ at anode|electrolyte interface. Accordingly, at a trace concentration of 0.01 mg mL‐1 ATU, these features endow Zn anode with a long cycling life (more than 800 h), and a high average Columbic efficiency (99.52%) for Zn||Cu batteries. When pairing with I2 cathode, the improved cycling ability (5000 cycles) with capacity retention of 77.9% is achieved. The fundamental understanding on the regulation of charge density at anode|electrolyte interface can facilitate the development of AZIBs.

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Supramolecular hydrogen-bonding network in 1-(diaminomethylene)thiouron-1-ium 4-hydroxybenzenesulfonate crystal

Cited by 11 publications

References 46 publications

Supramolecular hydrogen-bonding network in bis[1-(diaminomethylene)thiouron-1-ium] naphthalene-1,5-disulfonate

Supramolecular hydrogen-bonding network in bis[1-(diaminomethylene)thiouron-1-ium] naphthalene-1,5-disulfonate

Facile crystallization of 2-phenyl benzimidazole-5-sulfonic acid: Characterization of lattice water dependent zwitterionic supramolecular forms, with modulation in proton conductivities

Regulating the Interfacial Charge Density by Constructing a Novel Zn Anode‐Electrolyte Interface for Highly Reversible Zn Anode

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