(Di)-aminoguanidine Functionalization through Transamination: An Avenue to an Auspicious Class of Supramolecular Synthons

Naik, Anil D.; Tinant, Bernard; Léonard, A.; Marchand‐Brynaert, Jacqueline; Su, Bao‐Lian; Garcia, Yann

doi:10.1021/cg200612j

Cited by 12 publications

(10 citation statements)

References 66 publications

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“…The angles around the zinc atom deviate little from an ideal tetrahedron (109°) as they range from 104.02(10) to 115.12(10)°. The interatomic interactions are based on the linkage of one complex to four adjacent complex units through N−H ⋅⋅⋅ N hydrogen bonds with lengths of 2.117(3) and 2.170(3) Å, respectively …”

Section: Resultssupporting

confidence: 74%

“…The Zn−N distances are similar, the average value being 2.008 Å. This value is in the expected range and in good accordance with literature values for Zn−N distances in TzH‐containing compounds like [ZnL 2 Cl 2 ]⋅H 2 O (L=3,4‐diamino‐1,2,4‐1 H ‐triazole hydrochloride) . The angles around the zinc atom deviate little from an ideal tetrahedron (109°) as they range from 104.02(10) to 115.12(10)°.…”

Section: Resultsmentioning

confidence: 99%

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Mechanochemical Synthesis of 3d Transition‐Metal–1,2,4‐Triazole Complexes as Precursors for Microwave‐Assisted and Thermal Conversion to Coordination Polymers with a High Influence on the Dielectric Properties

Brede

Heine

Sextl

et al. 2016

Chemistry A European J

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The complexes [MCl2 (TzH)4] (M=Mn (1), Fe (2); TzH=1,2,4-1H-triazole) and [ZnCl2 (TzH)2] (3) have been obtained by mechanochemical reactions of the corresponding divalent metal chloride and 1,2,4-1H-triazole. They were successfully used as precursors for the formation of coordination polymers either by a microwave-assisted reaction or by thermal conversion. For manganese, the conversion directly yielded 1∞ [MnCl2 TzH] (4), whereas for the iron-containing precursor, 1∞ [FeCl2 TzH] (6), was formed via the intermediate coordination polymer 1∞ [FeCl(TzH)2]Cl (5). For cobalt, the isotypic polymer 1∞ [CoCl(TzH)2]Cl (7) was obtained, but exclusively by a microwave-induced reaction directly from CoCl2 . The crystal structures were resolved from single crystals and powders. The dielectric properties were determined and revealed large differences in permittivity between the precursor complexes and the rigid chain-like coordination polymers. Whereas the monomeric complexes exhibit very different dielectric behaviour, depending on the transition metal, from "low-k" to "high-k" with the permittivity ranging from 4.3 to >100 for frequencies of up to 1000 Hz, the coordination polymers and complexes with strong intermolecular interactions are all close to "low-k" materials with very low dielectric constants up to 50 °C. Therefore, the conversion procedures can be used to deliberately influence the dielectric properties from complex to polymer and for different 3d transition-metal ions.

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Section: Resultssupporting

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Mechanochemical Synthesis of 3d Transition‐Metal–1,2,4‐Triazole Complexes as Precursors for Microwave‐Assisted and Thermal Conversion to Coordination Polymers with a High Influence on the Dielectric Properties

Brede

Heine

Sextl

et al. 2016

Chemistry A European J

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“…As function is always related to three-dimensional structure, the quest for supramolecular synthons in three-dimensional networks is one of the main aims of crystal engineers to understand and explore the principles involved in the formation of that particular structure. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] The acquired knowledge can then be used for the deliberate design of novel crystalline materials with desired properties. [21][22][23][24][25][26] For this purpose, however, highly consistent synthons with sufficiently directional intermolecular forces are required.…”

Section: Introductionmentioning

confidence: 99%

Robustness of thioamide dimer synthon, carbon bonding and thioamide–thioamide stacking in ferrocene-based thiosemicarbazones

et al. 2015

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“…However, DATr as a ligand has seldom been studied. The synthesis and crystal structure of Zn(DATr) 2 Cl 2 was investigated and the complex is biologically relevant [32]. Our group reported the synthesis and some energetic properties of several metal complexes based on 3,4-diamino-1,2,4-triazole [33].…”

Section: Introductionmentioning

confidence: 99%

A 1D cadmium complex with 3,4-diamino-1,2,4-triazole as ligand: synthesis, molecular structure, characterization, and theoretical studies

Jin

Yin

et al. 2015

Journal of Coordination Chemistry

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2015): A 1D cadmium complex with 3,4-diamino-1,2,4-triazole as ligand: Synthesis, molecular structure, characterization, and theoretical studies, Journal of Coordination Chemistry, An energetic complex, [Cd 2 (μ-Cl) 4 Cl 2 (DATr) 2 ] n (1) (DATr = 3,4-diamino-1,2,4-triazole), was synthesized from DATr·HCl and cadmium(II) chloride. The product was characterized by Fourier transform-infrared spectroscopy (FT-IR) analysis, elemental analysis, X-ray diffraction analysis, and differential scanning calorimeter (DSC) analysis. The central cadmium(II) ions in 1 are six-coordinate twisted octahedral structures, which are made up of 1D chains linked by bridging chlorides. The results of the DSC analysis suggest the temperature of decomposition to be above 503.15 K. Furthermore, the kinetic properties of decomposition are studied by Kissinger's and Ozawa-Doyle's methods, and the calculated average activation is 166.5 kJ·mol -1 , which means the complex is stable under normal conditions. In addition, the energy of combustion was measured by oxygen bomb calorimetry. The critical temperature of thermal explosion and parameters of thermodynamics of 1 were calculated. The periodic structure of 1 has been calculated based on the density functional theory. The theoretical results explain the electronic structure and thermal dynamic properties.

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(Di)-aminoguanidine Functionalization through Transamination: An Avenue to an Auspicious Class of Supramolecular Synthons

Cited by 12 publications

References 66 publications

Mechanochemical Synthesis of 3d Transition‐Metal–1,2,4‐Triazole Complexes as Precursors for Microwave‐Assisted and Thermal Conversion to Coordination Polymers with a High Influence on the Dielectric Properties

Mechanochemical Synthesis of 3d Transition‐Metal–1,2,4‐Triazole Complexes as Precursors for Microwave‐Assisted and Thermal Conversion to Coordination Polymers with a High Influence on the Dielectric Properties

Robustness of thioamide dimer synthon, carbon bonding and thioamide–thioamide stacking in ferrocene-based thiosemicarbazones

A 1D cadmium complex with 3,4-diamino-1,2,4-triazole as ligand: synthesis, molecular structure, characterization, and theoretical studies

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