Theoretical study on the two novel planar-type all-nitrogen N44− anions: Structures, stability, reaction rate and their stable mechanisms via protonation

Feng, Yifan; Zhu, Haiyan; Zhang, Qiyan; Zhao, Qingzhong; Zhao, He; Suo, Bingbing; Zhai, Gaohong; Zou, Wenli; Huang, Han; Song, Qi; Li, Jianfu; Li, Yawei

doi:10.1016/j.cplett.2021.138519

Cited by 3 publications

(1 citation statement)

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“…Compounds of type C are represented in the literature as anions of unannulated and annulated 1,2,3-triazole 2-oxides and tetrazole 2-oxides. Type D acyclic anions are not described (for theoretical studies of such systems, see [ 2 ]), and type E anions are represented by compounds 1 [ 3 ] and 2 [ 4 ], in which three of the four atoms of the tripoid conjugated system are built into a five-membered heterocyclic ring ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

et al. 2022

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A strategy for the synthesis of 5-((2-cyanoethyl)-X-amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides (X = H; CH2CH2CN; NO2 (4a); CN (4b); CO2Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy is the intramolecular thermolytic cyclization of the azido group and the bis(2-cyanoethyl)triazene group. Removal of the 2-cyanoethyl protecting group from amides 4a–c gave potassium salt of the corresponding nitramide and sodium salts of cyano- and ethoxycarbonylamide. The structure and thermal stability of the synthesized compounds were studied experimentally using multinuclear NMR spectroscopy, X-ray crystallography, thermogravimetry, and differential scanning calorimetry.

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Section: Introductionmentioning

confidence: 99%

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

et al. 2022

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Theoretical Prediction and Comprehensive Characterization of an All‐Nitrogenatomic Ring, Cyclo[18]Nitrogen (N₁₈)

2024

ChemPhysChem

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The cyclic molecule cyclo[18]carbon composed of 18 carbon atoms has been observed in condensed phase experiment in recent years and has attracted great attention. Through state‐of‐art quantum chemistry calculation, this study found that 18 nitrogen atoms can also form a macrocyclic system, cyclo[18]nitrogen (N18), though its lifetime is very short at room temperature and can only exist for a relatively long time at very low temperatures. We comprehensively theoretically studied properties of N18, including geometric configurations, thermal decomposition mechanism and rate, molecular dynamics behavior, energetic properties, vibrational and electronic spectra. We also discussed in depth the electronic structure of N18, including nature of the N‐N bonds, lone‐pairs, charge distribution characteristics, electronic delocalization, and aromaticity. This work is not only the first exploration of the macrocyclic N18 molecule, but also the first time to systematically examine a very long‐chain substance fully composed of nitrogen atoms in isolated state.

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Hydrazine Oxidation in Aqueous Solutions II: N₄H₄ Decomposition

Breza,

Gatial

2024

ChemistrySelect

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The reaction mechanism for the N2H4 homogeneous oxidation in aqueous solutions is more complex than its heterogeneous electrochemical oxidation on the electrode surfaces. Homogenous oxidation of a mixture of non‐labeled (14N2H4) and 15N‐labeled (15N2H4) hydrazine in aqueous solutions produces 14N15N, indicating the intermediate existence of N4H6 or N4H4 intermediates with subsequent hydrogen transfers and splitting lateral N─N bonds. To explain the key part of the hydrazine oxidation reaction, the structures, thermodynamics, and electron characteristics of N4H4 in aqueous solution are investigated. Unlike N4H6, we have not found any spontaneous splitting of the bond between the lateral nitrogens in N4H4. The most probable products of N4H4 disproportionation are H2N─NH2 and N2, which are obtained by splitting the bond between the central nitrogen atoms, and so only 15N2 and 14N2 molecules are formed. Additionally, the formation of H3N─NH and N2 products is also preferred to structures without N─N fissions. The formation of H2N═N and HN═NH is energetically less advantageous. Cyclo‐N4H4 structures are stable, without any N─N fissions, but their energies indicate their vanishing abundance in aqueous solution, so their involvement in hydrazine oxidation is highly improbable. Unlike N4H6, the oxidation of hydrazine to 14N15N molecules cannot be explained by N4H4 intermediates.

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Theoretical study on the two novel planar-type all-nitrogen N44− anions: Structures, stability, reaction rate and their stable mechanisms via protonation

Cited by 3 publications

References 45 publications

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

Theoretical Prediction and Comprehensive Characterization of an All‐Nitrogenatomic Ring, Cyclo[18]Nitrogen (N₁₈)

Hydrazine Oxidation in Aqueous Solutions II: N₄H₄ Decomposition

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Theoretical study on the two novel planar-type all-nitrogen N44− anions: Structures, stability, reaction rate and their stable mechanisms via protonation

Cited by 3 publications

References 45 publications

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

Anions Containing Tripoid Conjugated N4− System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability

Theoretical Prediction and Comprehensive Characterization of an All‐Nitrogenatomic Ring, Cyclo[18]Nitrogen (N18)

Hydrazine Oxidation in Aqueous Solutions II: N4H4 Decomposition

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Theoretical Prediction and Comprehensive Characterization of an All‐Nitrogenatomic Ring, Cyclo[18]Nitrogen (N₁₈)

Hydrazine Oxidation in Aqueous Solutions II: N₄H₄ Decomposition