Synthesis of N-(Anthracen-9-ylmethyl)-N-methyl-2-(phenylsulfonyl)ethanamine via Microwave Green Synthesis Method: X-ray Characterization, DFT and Hirshfeld Analysis

Al-Qubati, Mohyeddine; Ghabbour, Hazem A.; Soliman, Saied M.; Al‐Majid, Abdullah Mohammed; Barakat, Assem; Sultan, Mujeeb A.

doi:10.3390/cryst10080643

Cited by 3 publications

(1 citation statement)

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“…The synthesis of new molecules and the elucidation of their molecular and supramolecular structures via single-crystal X-ray diffraction analysis are topics of great interest. We have previously studied ethanoanthracenes and published several articles in this field, which have been shown the biological importance of these compounds [23][24][25][26][27]. In this paper, we syntheize and elucidate the molecular and supramolecular structures of 1,8-dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Single Crystal X-ray, Hirshfeld and DFT Studies of 1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic Acid

Altowyan

Sultan²,

Soliman

et al. 2021

Crystals

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In this paper, synthesis, single-crystal X-ray structure, Hirshfeld and DFT studies of 1,8-dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic acid are discussed. Different intermolecular contacts affecting the crystal stability are studied using Hirshfeld calculations. The H…Cl and O…H contacts are the most significant, showing corresponding interaction distances of 2.731 Å (Cl2…H10) and 1.681Å (H1…O1), 2.328 Å (O1…H13), 2.510 Å (O1…H12) based on Hirshfeld calculations. DFT calculations are carried out to study the electronic behavior, as well as the 1H- and 13C-NMR spectra of the synthesized compound. The computed NMR chemical shifts show excellent correlation with the experimental data (R2 = 0.9884–0.9705).

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Section: Introductionmentioning

confidence: 99%

Synthesis, Single Crystal X-ray, Hirshfeld and DFT Studies of 1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic Acid

Altowyan

Sultan²,

Soliman

et al. 2021

Crystals

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Crystal structure, Hirshfeld surface analysis and computational study of three 2-(4-arylthiazol-2-yl)isoindoline-1,3-dione derivatives

Ghabbour

Fahim²,

El‐Enin

et al. 2022

Molecular Crystals and Liquid Crystals

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Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function

et al. 2020

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The 1,3-dipolar cycloaddition reaction is one of the most rapid, and efficient protocols to access, and construct highly divergent heterocycle chiral auxiliaries. Free catalyst synthesis of spirooxindole scaffold incorporating sulphone moiety via one pot–three component reaction of 6-chloro-isatin, L-proline, and the phenylvinylsulphone as dienophile is presented. The new regioisomer and diastereomer was isolated by precipitation without the tedious purification step, and then characterized via NMR and single crystal X-ray diffraction analysis. Using Hirshfeld analysis, the analysis of molecular packing was performed. It depended mainly on strong O…H and N…H interactions, and weak H…H, C…H, and Cl…H interactions as well. DFT calculations were used to optimize the experimental X-ray structure, which was found well matched with the calculated one. Reactivity descriptors based on the energies of the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals were calculated. Additionally, the donor–acceptor interactions which stabilized the system via σ–σ*, π→π*, n→σ* and n→π* electron delocalization processes were also computed using NBO calculations. The net interaction energies are 49.96, 235.38, 179.66 and 107.06 kJ/mol, respectively. Additionally, the calculated NMR chemical shifts correlated well with the experimental data (R2=0.99).

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Synthesis of N-(Anthracen-9-ylmethyl)-N-methyl-2-(phenylsulfonyl)ethanamine via Microwave Green Synthesis Method: X-ray Characterization, DFT and Hirshfeld Analysis

Cited by 3 publications

References 31 publications

Synthesis, Single Crystal X-ray, Hirshfeld and DFT Studies of 1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic Acid

Synthesis, Single Crystal X-ray, Hirshfeld and DFT Studies of 1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic Acid

Crystal structure, Hirshfeld surface analysis and computational study of three 2-(4-arylthiazol-2-yl)isoindoline-1,3-dione derivatives

Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function

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