A1 Journal article (refereed)
Intramolecular Hydrogen Bond, Hirshfeld Analysis, AIM; DFT Studies of Pyran-2,4-dione Derivatives (2021)

Boraei, A. T. A., Haukka, M., Sarhan, A. A. M., Soliman, S. M., & Barakat, A. (2021). Intramolecular Hydrogen Bond, Hirshfeld Analysis, AIM; DFT Studies of Pyran-2,4-dione Derivatives. Crystals, 11(8), Article 896. https://doi.org/10.3390/cryst11080896

JYU authors or editors

Publication details

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

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2021

Publication date: 30/07/2021

Volume: 11

Issue number: 8

Article number: 896

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst11080896

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/77282

Abstract

Intra and intermolecular interactions found in the developed crystals of the synthesized py-ron-2,4-dione derivatives play crucial rules in the molecular conformations and crystal stabili-ties, respectively. In this regard, Hirshfeld calculations were used to quantitatively analyze the different intermolecular interactions in the crystal structures of some functionalized py-ran-2,4-dione derivatives. The X-ray structure of pyran-2,4-dione derivative namely (3E,3′E)-3,3′-((ethane-1,2-diylbis(azanediyl))bis(phenylmethanylylidene))bis(6-phenyl-2H-pyran-2,4(3H)-dione) was determined. It crystallized in the monoclinic crystal system and C2/c space group with unit cell parameters: a = 14.0869(4) Å, b = 20.9041(5) Å, c = 10.1444(2) Å and β = 99.687(2)°. Generally, the H…H, H…C, O…H and C…C contacts are the most important interactions in the molecular packing of the studied pyran-2,4-diones. The molecular structure of these compounds is stabilized by intramolecular O…H hydrogen bond. The nature and strength of the O…H hy-drogen bonds were analyzed using atoms in molecules calculations. In all compounds, the O…H hydrogen bond belongs to closed-shell interactions where the interaction energies are higher at the optimized geometry than the X-ray one due to the shortening in the A…H distance as a con-sequence of the geometry optimization. These compounds have polar characters with different charged regions which explored using molecular electrostatic potential map. Their natural charges, reactivity descriptors and NMR chemical shifts were computed, discussed and compared.

Keywords: crystals; atoms; chemical bonds; organic compounds

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

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2021

JUFO rating: 1