A1 Journal article (refereed)
Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function (2020)


Al-Majid, Abdullah M.; Soliman, Saied M.; Haukka, Matti; Ali, M.; Islam, Mohammad S.; Shaik, Mohammed R.; Barakat, Assem (2020). Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function. Symmetry, 12 (8), 1337. DOI: 10.3390/sym12081337


JYU authors or editors


Publication details

All authors or editors: Al-Majid, Abdullah M.; Soliman, Saied M.; Haukka, Matti; Ali, M.; Islam, Mohammad S.; Shaik, Mohammed R.; Barakat, Assem

Journal or series: Symmetry

eISSN: 2073-8994

Publication year: 2020

Volume: 12

Issue number: 8

Article number: 1337

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/sym12081337

Open Access: Publication published in an open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/71828


Abstract

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).


Keywords: organic compounds; aromatic compounds; sulphur compounds; isomerism

Free keywords: spirooxindole; sulphone; 1,3-dipolar cycloaddition reaction; regioisomer; diastereomer; Hirshfeld analysis


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Ministry reporting: Yes

Preliminary JUFO rating: 1


Last updated on 2020-21-09 at 17:12