A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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-tekijät tai -toimittajat

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Al-Majid, Abdullah M.; Soliman, Saied M.; Haukka, Matti; Ali, M.; Islam, Mohammad S.; Shaik, Mohammed R.; Barakat, Assem

Lehti tai sarja: Symmetry

eISSN: 2073-8994

Julkaisuvuosi: 2020

Volyymi: 12

Lehden numero: 8

Artikkelinumero: 1337

Kustantaja: MDPI

Julkaisumaa: Sveitsi

Julkaisun kieli: englanti

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

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/71828

Tiivistelmä

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).

YSO-asiasanat: orgaaniset yhdisteet; aromaattiset yhdisteet; rikkiyhdisteet; isomeria

Vapaat asiasanat: spirooxindole; sulphone; 1,3-dipolar cycloaddition reaction; regioisomer; diastereomer; Hirshfeld analysis

Liittyvät organisaatiot

OKM-raportointi: Kyllä

VIRTA-lähetysvuosi: 2020

JUFO-taso: 1