Molecular structure, covalent and non-covalent interactions of an oxaborole derivative (L-PRO2F3PBA): FTIR, X-ray diffraction and QTAIM approach

In this work, we have performed a computational study using the B3LYP/6‐31G(d,p) density functional theory (DFT) method of the solvent effects, the mechanism and the selectivity of the cationic imino‐Diels–Alder cycloaddition reaction between in situ‐generated cationic 2‐azadienes and arylpropenes. This reaction proceeds via a stepwise mechanism, in which the first step is the rate determining, favouring kinetically and thermodynamically the formation of the cycloadduct generated from meta‐exo approach. Analysis of different solvent effects indicates that the low polar solvents are the best solvents for this kind of reaction. The global reactivity descriptors indicates that the dienimine 1 is a strong electrophile, whereas, ethylene 2 is a good nucleophile. The local reactivity descriptors explain the obtained experimental meta regioselectivity. The NCI analysis indicates the presence of different favourable non‐covalent interactions, while QTAIM analysis indicates that steric hindrance at the meta‐endo approach is the origin for the experimentally observed meta‐exo stereoselectivity. The obtained results are in agreement with the experimental data.

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The effects of solvent nature and steric hindrance on the reactivity, mechanism and selectivity of the cationic imino‐Diels–Alder cycloaddition reaction between cationic 2‐azadienes and arylpropene

Sadi

Nacereddine

Djerourou

2022

J of Physical Organic Chem

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Nitronium salts as mild and inexpensive oxidizing reagents toward designing efficient strategies in organic syntheses; A mechanistic investigation based on the DFT insights

Sabet‐Sarvestani

Bolourian

Hosseini

et al. 2022

Journal of Molecular Graphics and Modelling

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New hydrate cocrystal of l-proline with 4-acetylphenylboronic acid obtained via mechanochemistry and solvent evaporation: An experimental and theoretical study

Hernández-Negrete

Sotelo‐Mundo

Ponce

et al. 2022

Journal of Solid State Chemistry

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Molecular structure, covalent and non-covalent interactions of an oxaborole derivative (L-PRO2F3PBA): FTIR, X-ray diffraction and QTAIM approach

Cited by 5 publications

References 76 publications

The effects of solvent nature and steric hindrance on the reactivity, mechanism and selectivity of the cationic imino‐Diels–Alder cycloaddition reaction between cationic 2‐azadienes and arylpropene

The effects of solvent nature and steric hindrance on the reactivity, mechanism and selectivity of the cationic imino‐Diels–Alder cycloaddition reaction between cationic 2‐azadienes and arylpropene

Nitronium salts as mild and inexpensive oxidizing reagents toward designing efficient strategies in organic syntheses; A mechanistic investigation based on the DFT insights

New hydrate cocrystal of l-proline with 4-acetylphenylboronic acid obtained via mechanochemistry and solvent evaporation: An experimental and theoretical study

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