Intra- and Intermolecular Interactions in the Crystals of 3,4-Diamino-1,2,4-triazole and Its 5-Methyl Derivative. Experimental and Theoretical Investigations of Charge Density Distribution

Konovalova, Irina S.; Nelyubina, Yulia V.; Paponov, B. V.; Шишкин, Олег В.

doi:10.1021/jp203732h

Cited by 22 publications

(19 citation statements)

References 69 publications

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“…The computed topological parameters at CH…O were in the range of 0.014–0.006 a.u. This value falls in the range of hydrogen bonding, predicted in previous studies . The electron density at N…Cl and C…Cl type BCPs are close to 0.007 a.u, while C…Cl type and O…S type has 0.006 and 0.004 a.u., respectively.…”

Section: Resultssupporting

confidence: 75%

Computational study on the interactions of mustard gas with cucurbituril macrocycles

Venkataramanan

Suvitha

Mizuseki

et al. 2015

Int J of Quantum Chemistry

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The study on the absorption of toxic gases such as mustard gas by organic host is essential to the development of inexpensive detection and decontamination equipments. Using quantum chemical methods, we propose cucurbituril as an effective host to capture mustard gas. It was found that stable complexes are formed with the inclusion of the toxic gas molecules inside the cucurbituril cavity, compared with the lateral and exterior interactions. Oxygen mustard has a comparable binding energy with sulfur mustard and hence can be used during experimental investigation. Additionally, during the inclusion complex formation, the presence of heteroatoms helps the guest molecules to undergo a larger structural reorganization to get accommodated inside the cucurbituril macromolecule. Atoms‐in‐molecules analysis shows the existence of strong intermolecular CH…O bonding between the guest molecules and cucurbituril macromolecule. The presence of an intramolecular CH…Cl type of bonding accounts for the higher stabilization of sulfur mustard inside the cucurbituril macromolecule. © 2015 Wiley Periodicals, Inc.

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Section: Resultssupporting

confidence: 75%

Computational study on the interactions of mustard gas with cucurbituril macrocycles

Venkataramanan

Suvitha

Mizuseki

et al. 2015

Int J of Quantum Chemistry

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“…These distances are much longer than those found in similar coordination compounds[39]. Metal coordination has slightly changed the bond lengths of N-N and C-N bonds of the triazole ring[31].Bond angles of two trans chlorides and cadmium ions as well as the bond angles of N-Cd-Cl (the trans chloride to 1,2,4-triazole ring) deviate from 180°, which results in a distorted octahedral configuration. The torsion angle of Cl(1A)-Cd(1)-Cl(1)-Cd(1A) is 0°, which suggests that Cd1, Cd1A, Cl1 and Cl1A form a rhombus geometry with the equation of plane A: 4.083x -8.946y + 1.813z = 18.485.…”

mentioning

confidence: 75%

“…DATr has been described in the literature [30,31]. However, DATr as a ligand has seldom been studied.…”

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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“…structure of compounds can be obtained from the distribution of electron density, in particular, from its Laplacian r 2 (r) (Bushmarinov et al, 2008;Konovalova et al, 2011;Nelyubina & Lyssenko, 2013). The electrons are concentrated in regions, where r 2 (r) < 0, and are deconcentrated, where r 2 (r) > 0.…”

Section: Figurementioning

confidence: 99%

Twist-chair conformation of the tetraoxepane ring remains unchanged in tetraoxaspirododecane diamines

et al. 2020

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A detailed structural analysis has been performed for N,N′‐bis(4‐chlorophenyl)‐7,8,11,12‐tetraoxaspiro[5.6]dodecane‐9,10‐diamine, C20H22Cl2N2O4, (I), N,N′‐bis(2‐fluorophenyl)‐7,8,11,12‐tetraoxaspiro[5.6]dodecane‐9,10‐diamine, C20H22F2N2O4, (II), and N,N′‐bis(4‐fluorophenyl)‐7,8,11,12‐tetraoxaspiro[5.6]dodecane‐9,10‐diamine, C20H22F2N2O4, (III). The seven‐membered ring with two peroxide groups adopts a twist‐chair conformation in all three compounds. The lengths of the C—N and O—O bonds are slightly shorter than the average statistical values found in the literature for azepanes and 1,2,4,5‐tetraoxepanes. The geometry analysis of compounds (I)–(III), the topological analysis of the electron density at the (3, −1) bond critical points within Bader's quantum theory of `Atoms in molecules' (QTAIM) and NBO (natural bond orbital) analysis at the B3LYP/6‐31G(d,2p) level of theory showed that there are nO→σ*(C—O), nN→σ*(C—O) and nO→σ*(C—N) stereoelectronic effects. The molecules of compounds (I) and (III) are packed in the crystals as zigzag chains due to strong N—H…O and C—H…O hydrogen‐bond interactions, whereas the molecules of compound (II) form chains in the crystals bound by N—H…O, C—H…π and C—H…O contacts. All these data show that halogen atoms and their positions have a minimal effect on the geometric parameters, stereoelectronic effects and crystal packing of compounds (I)–(III), so that the twist‐chair conformation of the tetraoxepane ring remains unchanged.

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Intra- and Intermolecular Interactions in the Crystals of 3,4-Diamino-1,2,4-triazole and Its 5-Methyl Derivative. Experimental and Theoretical Investigations of Charge Density Distribution

Cited by 22 publications

References 69 publications

Computational study on the interactions of mustard gas with cucurbituril macrocycles

Computational study on the interactions of mustard gas with cucurbituril macrocycles

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

Twist-chair conformation of the tetraoxepane ring remains unchanged in tetraoxaspirododecane diamines

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