Role of hydrogen bonding interactions within of the conformational preferences of calix[n = 4,6,8]arene: DFT and QTAIM analysis

Gassoumi, Bouzid; Chaabéne, Marwa; Ghalla, Houcine; Chaâbane, Rafik Ben

doi:10.1007/s00894-019-4255-5

Cited by 8 publications

(7 citation statements)

References 30 publications

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“…The topological parameters obtained here are consistent with hydrogen bond interactions observed in previous studies [39,40]. The larger hydrogen-bonding interaction energies calculated for 2 E int (BSSE) = −11.782 kcal mol vs. 1 (E int (BSSE) = −11.465 kcal/mol) are also consistent with the shorter intermolecular distances observed in the crystal structures.…”

Section: Resultssupporting

confidence: 91%

“…As shown in Tables 3 and S1, this BCP also presented QTAIM parameters very similar to those observed for Br•••Br contacts, which indicates a vdW attractive interaction. The topological parameters obtained here are consistent with hydrogen bond interactions observed in previous studies [39,40] The topological parameters obtained here are consistent with hydrogen bond interactions observed in previous studies [39,40] A Br•••Br interaction dimer was investigated for structures 1 (1-BrBr) and 2 (2-CHBrBr). Although no short Br•••Br contacts are present in 2, bond critical points (BCPs) were observed in the theoretical calculations.…”

Section: Resultssupporting

confidence: 90%

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Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions

et al. 2021

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X-ray structural determinations and computational studies were used to investigate halogen interactions in two halogenated oxindoles. Comparative analyses of the interaction energy and the interaction properties were carried out for Br···Br, C-H···Br, C-H···O and N-H···O interactions. Employing Møller–Plesset second-order perturbation theory (MP2) and density functional theory (DFT), the basis set superposition error (BSSE) corrected interaction energy (Eint(BSSE)) was determined using a supramolecular approach. The Eint(BSSE) results were compared with interaction energies obtained by Quantum Theory of Atoms in Molecules (QTAIM)-based methods. Reduced Density Gradient (RDG), QTAIM and Natural bond orbital (NBO) calculations provided insight into possible pathways for the intermolecular interactions examined. Comparative analysis employing the electron density at the bond critical points (BCP) and molecular electrostatic potential (MEP) showed that the interaction energies and the relative orientations of the monomers in the dimers may in part be understood in light of charge redistribution in these two compounds.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 90%

Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions

et al. 2021

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“…The stable structures of the studied systems (CX [4] and CX[4]-gas) have been calculated with the DFT method by using the B3LYP [16,[19][20][21] coupled to the D3BJ (empirical Becke and Johnson damping dispersion corrections) in combination with the 6-31 + G(d) basis set, as implemented in GAUSSIAN 09 package [22] and the Gauss View [23] as a visual program. We have been calculated the binding energies of the CX[4]-gas take into account the Basis Set Superposition Error (BSSE) counterpoise (CP) correction energy of Boys and Bernardi [24].…”

Section: Methodsmentioning

confidence: 99%

Possibility of Complexation of the Calix[4]Arene Molecule with the Polluting Gases: DFT and NCI-RDG Theory

Gassoumi¹,

Mohamed²,

Ghalla³

et al. 2021

Environmental Issues and Sustainable Development

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The calix[4]arenes (abbreviated as CX[4]) are characterized by a specific hydrophobic cavity formed by a four cyclically phenol groups to encapsulate a gas or small molecules. Recently, the CX[4] molecule is used in a specific media and in pharmaceutical drug delivery. The pollution problem will be a vital subject in the future because the increase of the explosions of the gaseous pollutants in the environment. In this report, we have encapsulated the polluting gases NO3, NO2, CO2 and N2 by the calix[4]arene molecule. In this work, The binding energies of the CX[4]-gas has been calculated including the BSSE (Basis Set Superposition Error) counterpoise (CP). The red-shift of the O-H bonding interactions obtained by adding the gas in the sensitive area of calix[4]arene is clearly explained by the infrared spectrum analysis. The Molecular electrostatic potential (MEP) of the stable CX[4]-gas complexes have been investigated in the endo-vs. exo-cavity regions. Finally, the non-covalent interactions analyses of the stable host-guests complexes have been estimated by using DFT calculations.

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“…The optimization of CX [4] and CX [4]-gas have been performed by the Density Functional Theory (DFT) method by using the global hybrid generalized gradient approximation B3LYP [15,18,19,20] coupled to the D3BJ (empirical Becke and Johnson damping dispersion corrections) in combination with the 6-31þG(d) basis set, as implemented in a Gaussian 09 package [21] and the GaussView [22] as a visual program. The binding energies have been calculated taking into account the Basis Set Superposition Error (BSSE) counterpoise correction (CP) according to the formalism of Boys and Bernardi [23].…”

Section: Computational Detailsmentioning

confidence: 99%

A theoretical study of the global and local electrophilicity, nucleophilicity, polarizability and QTAIM theory for calix[4]arene-gas interaction

Gassoumi

Ghalla

Chaâbane

2020

Heliyon

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The calix[4]arene molecule, abbreviated as CX[4], is known by the four phenolic groups and a hydrophobic cavity able to enclose small molecules. The interactions between CX[4] and NO 3, NO 2 , CO 2 , and N 2 gas molecules have been studied. These guest species are placed inside and outside the cavity of the host molecule CX[4]. The formation of H-bonding has been deeply discussed based on the infrared spectrum and the polarizability analysis. Global and local indices have been calculated for a series of gas (NO 3, NO 2 , CO 2 and N 2 ) in interaction with the CX[4] molecule to explain the electrophilic or nucleophilic activations in endo-vs. exo-cavity interaction zone. As expected, there is a correlation between the proposed global electrophilicity and global nucleophilicity together for an explanation of the chemo-selectivity region. Finally, the topological parameter analyses of the host-guests interactions have been estimated by using DFT calculations.

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Role of hydrogen bonding interactions within of the conformational preferences of calix[n = 4,6,8]arene: DFT and QTAIM analysis

Cited by 8 publications

References 30 publications

Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions

Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions

Possibility of Complexation of the Calix[4]Arene Molecule with the Polluting Gases: DFT and NCI-RDG Theory

A theoretical study of the global and local electrophilicity, nucleophilicity, polarizability and QTAIM theory for calix[4]arene-gas interaction

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