Dibenzothiophene adsorption at boron doped carbon nanoribbons studied within density functional theory

López-Albarrán, Pablo; Navarro-Santos, Pedro; García-Ramírez, Mario Alberto; Ricardo-Chávez, J. L.

doi:10.1063/1.4922452

Cited by 5 publications

(2 citation statements)

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“…This fact is probably due to both of the nearest B atoms to C having one unoccupied π orbital, and then the lack of π electrons of the B – C – B atoms interacts strongly with the aromatic thiophene ring, which is in agreement with results of the MEP isosurfaces shown in Figure 5. Figure 7d shows the complex formed for the DBT on the BNNR_BC; note that the configurations of both aromatic organosulfur molecules considered in this work are tilted in such adsorbed states (~54°), which is in agreement with other complexes involving organosulfur compounds adsorbed on C-based doped nanomaterials [53].…”

Section: Resultssupporting

confidence: 82%

“…Based on previous reports, we know that the most reactive sites of the DBT are the sulfur atom (which may behave as a nucleophile) and its aromatic rings, which can also donate charge, and eventually their hydrogen atoms could accept charge [52,53,54]. Despite these facts, we built complexes between the organosulfur compounds and the C-doped BNNRs, considering several adsorption modes of the organosulfur compounds to explore their affinity on all the selected potentially active sites, i.e., when adsorption takes place through the sulfur atom perpendicularly oriented to the surface (namely, <<1>>).…”

Section: Resultsmentioning

confidence: 99%

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Reactivity of Atomically Functionalized C-Doped Boron Nitride Nanoribbons and Their Interaction with Organosulfur Compounds

et al. 2019

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The electronic and reactivity properties of carbon doped (C-doped) boron nitride nanoribbons (BNNRs) as a function of the carbon concentration were investigated in the framework of the density functional theory within the generalized gradient approximation. We found that the main routes to stabilize energetically the C-doped BNNRs involve substituting boron atoms near the edges. However, the effect of doping on the electronic properties depends of the sublattice where the C atoms are located; for instance, negative doping (partial occupations of electronic states) is found replacing B atoms, whereas positive doping (partial inoccupation of electronic states) is found when replacing N atoms with respect to the pristine BNNRs. Independently of the even or odd number of dopants of the C-doped BNNRs studied in this work, the solutions of the Kohn Sham equations suggest that the most stable solution is the magnetic one. The reactivity of the C-doped BNNRs is inferred from results of the dual descriptor, and it turns out that the main electrophilic sites are located near the dopants along the C-doped BNNRs. The reactivity of these nanostructures is tested by calculating the interaction energy between undesirable organosulfur compounds present in oil fuels on the C-doped BNNRs, finding that organosulfur compounds prefer to interact over nanosurfaces with dopants substituted on the B sublattice of the C-doped BNNRs. Most importantly, the selective C doping on the BNNRs offers the opportunity to tune the properties of the BNNRs to fit novel technological applications.

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Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Reactivity of Atomically Functionalized C-Doped Boron Nitride Nanoribbons and Their Interaction with Organosulfur Compounds

et al. 2019

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Conjugate addition between syringol and a captodative olefin catalyzed by BF3

Morales‐Palacios

Navarro-Santos

Beiza-Granados

et al. 2019

J of Physical Organic Chem

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The regioselectivity of the conjugate addition between syringol (1) and the captodative olefin 3‐(p‐nitrobenzoyloxy)‐but‐3‐en‐2‐one (2) is evaluated under diverse solvent and Lewis acid catalyst conditions, providing a mixture of the para/meta phenol adducts. Experimental results revealed for most of the trials that the para regioisomer is the major one. However, there is not a clear correlation between the regioselectivity of products and the polarity of the tested solvents. In this work, the reactivity descriptors and the reaction mechanism are studied in the framework of the density functional theory (DFT) to give insights about the reactivity and regioselectivity of this reaction. The Parr functions difference is used as the reactivity descriptor in each stage of the reaction explaining quite well the involved transition states. Overall, it is found that the reactivity of 1 is strongly influenced by the presence of the catalyst, while the regioselectivity of the products depends on both the catalyst and the polarity of the solvent, finding that, the meta adduct is highly dependent of the presence of nonpolar solvents.

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