A1 Journal article (refereed)
Synthesis of C2-Symmetrical Bis-(β-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and Bis-(Pyran-2,4-diones) Derivatives (2021)


Boraei, A. T. A., Haukka, M., Sarhan, A. A. M., Soliman, S. M., Al-Majid, A. M., & Barakat, A. (2021). Synthesis of C2-Symmetrical Bis-(β-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and Bis-(Pyran-2,4-diones) Derivatives. Symmetry, 13(9), Article 1646. https://doi.org/10.3390/sym13091646


JYU authors or editors


Publication details

All authors or editorsBoraei, Ahmed T. A.; Haukka, Matti; Sarhan, Ahmed A. M.; Soliman, Saied M.; Al-Majid, Abdullah Mohammed; Barakat, Assem

Journal or seriesSymmetry

eISSN2073-8994

Publication year2021

Publication date07/09/2021

Volume13

Issue number9

Article number1646

PublisherMDPI AG

Publication countrySwitzerland

Publication languageEnglish

DOIhttps://doi.org/10.3390/sym13091646

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/77817


Abstract

The synthesis of C2-symmetrical bis(β-enamino-pyran-2,4-dione) derivative 3 connected via 1,6-hexylene linker was reported for the first time. X-ray structures and Hirshfeld studies of the new bis- β-enamino-pyran-2,4-dione derivative 3 along with two structurally related pyran-2,4-dione derivatives 2a,b were discussed. A comparative analysis of the different intermolecular contacts affecting the crystal stability was presented. Generally, the H…H, O…H, and H…C interactions are common in all compounds and are considered the most abundant contacts. In addition, DFT calculations were used to compute the electronic properties as well as the 1H and 13C NMR spectra of the studied systems. All compounds (except 3) are polar where 2a (3.540 Debye) has a higher dipole moment than 2b (2.110 Debye). The NMR chemical shifts were calculated and excellent correlations between the calculated and experimental data were obtained (R2 = 0.93–0.94).


Keywordschemical synthesisorganic compoundshydrogen bondssymmetry

Free keywordspyran-2,4-dione; C2-symmetrical; Hirshfeld analysis; AIM; DFT; intramolecular hydrogen bond


Contributing organizations


Ministry reportingYes

Reporting Year2021

JUFO rating1


Last updated on 2024-25-03 at 09:24