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, A. M., Soliman, S. M., Haukka, M., Ali, M., Islam, M. S., Shaik, M. R., & Barakat, A. (2020). Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function. Symmetry, 12(8), Article 1337. https://doi.org/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
Publication open access: Openly available
Publication channel open access: 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
Contributing organizations
Ministry reporting: Yes
Reporting Year: 2020
JUFO rating: 1