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(external link)

JYU authors or editors

Publication details

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

Journal or series: Symmetry

eISSN: 2073-8994

Publication year: 2021

Publication date: 07/09/2021

Volume: 13

Issue number: 9

Article number: 1646

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/sym13091646(external link)

Publication open access: Openly available

Publication channel open access: Open Access channel

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

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).

Keywords: chemical synthesis; organic compounds; hydrogen bonds; symmetry

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

Contributing organizations

Ministry reporting: Yes

VIRTA submission year: 2021

JUFO rating: 1