Revisiting the formation mechanism of diarylamines via Smiles rearrangement

Murillo, Fernando; Quintal, Alan; Dzib, Eugenia; Zárate, Ximena; Fernández-Herrera, María A.; Merino, Gabriel

doi:10.1002/poc.4427

Cited by 2 publications

(2 citation statements)

References 23 publications

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“…We selected the synthesis of 4-nitrodiphenylamine from 4-nitro-N-phenylbenzenesulfinamide diarylsulfinamides as a test for the scan case [39,40]. The most favorable pathway for this reaction involves a concerted, base-catalyzed 3-exo-trig Smiles rearrangement, followed by the SO extrusion to form the corresponding diarylamine.…”

Section: Scan Case: Synthesis Of 4-nitrodiphenylamine From 4-nitro-n-...mentioning

confidence: 99%

SurfinPES: Performing automated analysis of activation strain, energy decomposition, and reaction force

Quintal¹,

Dzib²,

Murillo³

et al. 2023

Int J of Quantum Chemistry

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Analyzing activation strain, energy decomposition, and reaction force models is crucial for studying chemical reactivity and gaining quantitative insights into the factors that control energy barriers. However, manually preparing and processing the necessary data can be challenging and prone to errors. To address this issue, we introduce SurfinPES, a Python‐based module in Eyringpy that automates data extraction and processing for these analyses. SurfinPES also allows monitoring of the evolution of primitive properties (geometrical and electronic) along the reaction coordinate. The module is user‐friendly with a simple input format, making it accessible to any user in the field of computational chemistry.

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Section: Scan Case: Synthesis Of 4-nitrodiphenylamine From 4-nitro-n-...mentioning

confidence: 99%

SurfinPES: Performing automated analysis of activation strain, energy decomposition, and reaction force

Quintal¹,

Dzib²,

Murillo³

et al. 2023

Int J of Quantum Chemistry

Self Cite

View full text Add to dashboard Cite

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“…These experimental advancements motivated us to further investigate the potential applications of transition metal-HHTQ complexes in electrocatalytic CO 2 reduction. Theoretical advances in recent years have had a significant impact on research in physics, chemistry, and materials science [49][50][51]. In this study, we prepared a series of TM-HHTQ metal-organic frameworks containing transition 3d metals and carried out a comprehensive investigation of their electrocatalytic CO 2 reduction reaction (CO 2 RR) using density functional theory (DFT).…”

Section: Introductionmentioning

confidence: 99%

Exploring the CO2 Electrocatalysis Potential of 2D Metal–Organic Transition Metal–Hexahydroxytriquinoline Frameworks: A DFT Investigation

Wen,

Jiang,

Lai

et al. 2024

Molecules

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Metal–organic frameworks have demonstrated great capacity in catalytic CO2 reduction due to their versatile pore structures, diverse active sites, and functionalization capabilities. In this study, a novel electrocatalytic framework for CO2 reduction was designed and implemented using 2D coordination network-type transition metal–hexahydroxytricyclic quinazoline (TM–HHTQ) materials. Density functional theory calculations were carried out to examine the binding energies between the HHTQ substrate and 10 single TM atoms, ranging from Sc to Zn, which revealed a stable distribution of metal atoms on the HHTQ substrate. The majority of the catalysts exhibited high selectivity for CO2 reduction, except for the Mn–HHTQ catalysts, which only exhibited selectivity at pH values above 4.183. Specifically, Ti and Cr primarily produced HCOOH, with corresponding 0.606 V and 0.236 V overpotentials. Vanadium produced CH4 as the main product with an overpotential of 0.675 V, while Fe formed HCHO with an overpotential of 0.342 V. Therefore, V, Cr, Fe, and Ti exhibit promising potential as electrocatalysts for carbon dioxide reduction due to their favorable product selectivity and low overpotential. Cu mainly produces CH3OH as the primary product, with an overpotential of 0.96 V. Zn primarily produces CO with a relatively high overpotential of 1.046 V. In contrast, catalysts such as Sc, Mn, Ni, and Co, among others, produce multiple products simultaneously at the same rate-limiting step and potential threshold.

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Revisiting the formation mechanism of diarylamines via Smiles rearrangement

Cited by 2 publications

References 23 publications

SurfinPES: Performing automated analysis of activation strain, energy decomposition, and reaction force

SurfinPES: Performing automated analysis of activation strain, energy decomposition, and reaction force

Exploring the CO2 Electrocatalysis Potential of 2D Metal–Organic Transition Metal–Hexahydroxytriquinoline Frameworks: A DFT Investigation

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