On the question of the molecular mechanism of N-nitropyrazole rearrangement

Jasiński, Radomir

doi:10.1007/s10593-020-02799-x

Cited by 3 publications

(4 citation statements)

References 15 publications

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“…The PES data given in Figure 3 confirm these results. Also, it should be noted that TS (AB-3) could potentially be considered for the ( York and Bell, 2019 ; Herndon and Whiteside, 2021 )-proton-sigmatropic shift reaction due to properties which have recently been revealed in Jasiński, (2020 ). We have used the B3LYP/6311++G (d,p) level of theory for these mechanism studies due to the fact that this basis set has been widely applied for theoretical prediction of the experimentally investigated reaction parameters.…”

Section: Resultsmentioning

confidence: 99%

Carbon fixation of CO2 via cyclic reactions with borane in gaseous atmosphere leading to formic acid (and metaboric acid); A potential energy surface (PES) study

et al. 2022

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Carbon dioxide (CO2), a stable gaseous species, occupies the troposphere layer of the atmosphere. Following it, the environment gets warmer, and the ecosystem changes as a consequence of disrupting the natural order of our life. Due to this, in the present reasearch, the possibility of carbon fixation of CO2 by using borane was investigated. To conduct this, each of the probable reaction channels between borane and CO2 was investigated to find the fate of this species. The results indicate that among all the channels, the least energetic path for the reaction is reactant complex (RC) to TS (A-1) to Int (A-1) to TS (A-D) to formic acid (and further meta boric acid production from the transformation of boric acid). It shows that use of gaseous borane might lead to controlling these dangerous greenhouse gases which are threatening the present form of life on Earth, our beautiful, fragile home.

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Section: Resultsmentioning

confidence: 99%

Carbon fixation of CO2 via cyclic reactions with borane in gaseous atmosphere leading to formic acid (and metaboric acid); A potential energy surface (PES) study

et al. 2022

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“…15 Jasiński reported a two-step isomerization mechanism of the transformation of 3-methyl-1-nitro-1H-pyrazole into 3-methyl-5-nitro-1H-pyrazole. 16 It was reported that the different positions of the nitro groups affect the chemical and physical properties of the nitrated pyrazoles. 17 Ravi et al explored the isoconversional kinetics of decomposition of nitropyrazoles by using the TG-DTA technique and provided the clue of the decomposition mechanism.…”

Section: Introductionmentioning

confidence: 99%

“…During the synthetic progress, the unexpected isomerization of nitrated‐pyrazoles occurs 15 . Jasiński reported a two‐step isomerization mechanism of the transformation of 3‐methyl‐1‐nitro‐1 H ‐pyrazole into 3‐methyl‐5‐nitro‐1 H ‐pyrazole 16 . It was reported that the different positions of the nitro groups affect the chemical and physical properties of the nitrated pyrazoles 17 .…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on the structure and the isomerization mechanism of N‐nitropyrazole

Zhang¹,

Li²,

Xu³

et al. 2022

Int J of Chemical Kinetics

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N‐nitropyrazole, as a kind of important intermediate, is used to synthesize the novel energetic material. Therefore, it is necessary to get an insight into the isomerization mechanism. Herein, we propose three reaction pathways. Quantum chemistry theory was used to calculate the structure, energy, and thermal parameter. Pathway A is the main path with the lowest energy barrier. The theoretical rate constant is 0.022 min−1 which has a good agreement with the experimental result of 0.021 min−1. The proton shift was also studied to confirm that 2H‐3‐nitropyrazole is the final production.

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“…The migration of the nitro group in reactions plays an important role in the processes of transformation of organic compounds. Within this class of reactions, besides the nitro group rearrangement realized via [1.3]‐ 1,2 or [1.5]‐sigmatropic shift mechanisms, 3–6 many examples of nitrous acid extrusion were described. Most of these reactions proceed according to the β‐elimination scheme.…”

Section: Introductionmentioning

confidence: 99%

Understanding the molecular mechanism of γ‐elimination of nitrous acid in the framework of the molecular electron density theory

Kącka‐Zych

Jasiński

2021

J Comput Chem

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The reactions of γ-dehydronitration of furaxanenitrolic acids have been studied within the density functional theory using molecular electron density theory scheme at the MPWB1K(PCM)/6-311G(d,p) level of theory. The alteration of bonding along the course of the reaction is studied in the topology of the electron density functional within the bonding evolution theory perspective. The characteristics of electron density changes indicate that we can distinguish six different phases in the nitrous acid extrusion from furaxanenitrolic acid 1a. These different phases related to the intrinsic reaction coordinate path of the analyzed reaction denote the nonconcerted nature of the molecular mechanism.

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On the question of the molecular mechanism of N-nitropyrazole rearrangement

Cited by 3 publications

References 15 publications

Carbon fixation of CO2 via cyclic reactions with borane in gaseous atmosphere leading to formic acid (and metaboric acid); A potential energy surface (PES) study

Carbon fixation of CO2 via cyclic reactions with borane in gaseous atmosphere leading to formic acid (and metaboric acid); A potential energy surface (PES) study

Theoretical study on the structure and the isomerization mechanism of N‐nitropyrazole

Understanding the molecular mechanism of γ‐elimination of nitrous acid in the framework of the molecular electron density theory

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