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Research on Chemical Intermediates

, Volume 44, Issue 7, pp 4213–4225 | Cite as

New hybrid of the barbituric acid motif: synthesis, X-ray single crystal, DFT, and Hirshfeld surface analyses

  • Assem Barakat
  • M. Ali
  • Saied M. Soliman
  • Abdel-Moneim Abu-Elfotoh
  • Abdullah Mohammed Al-Majid
  • Hazem A. Ghabbour
Article

Abstract

A one-pot multi-component reaction of N,N-dimethylbarbituric acid,1,3-cyclohexanedione and 3-bromobenzaldehyde in H2O mediated by diethyl amine as a base affords a new barbituric acid–cyclohexanedione hybrid. The reaction proceeds smoothly, efficiently, and in high yield. The molecular structure of this compound was determined by single-crystal X-ray diffraction crystallography and spectrophotometric analyses. Of the nine possible isomers of the studied compound, the B3LYP/6-31G(d,p) method predicts that form B, in which the two OH groups are involved in significant intramolecular H-bonding interactions with the neighboring carbonyl O atom, is the most stable form in the gas phase. The X-ray structure reveals a different isomer due to intermolecular interactions caused by molecular packing in the crystal, which stabilizes the solid-state structure. Hirshfeld surface analysis of the molecular packing indicates that the H···O interactions are the primary contributor (24.5%) to the intermolecular stabilization in the crystal.

Keywords

Green chemistry Barbituric acid Cyclohexanedione DFT computation 

Notes

Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding this Research group No (RGP-044).

Supplementary material

11164_2018_3364_MOESM1_ESM.docx (549 kb)
Supplementary material 1 (DOCX 549 kb)

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Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  • Assem Barakat
    • 1
    • 3
  • M. Ali
    • 1
  • Saied M. Soliman
    • 2
  • Abdel-Moneim Abu-Elfotoh
    • 2
    • 4
  • Abdullah Mohammed Al-Majid
    • 1
  • Hazem A. Ghabbour
    • 5
    • 6
  1. 1.Department of Chemistry, College of ScienceKing Saud UniversityRiyadhSaudi Arabia
  2. 2.Department of ChemistryRabigh College of Science and ArtRabighSaudi Arabia
  3. 3.Department of Chemistry, Faculty of ScienceAlexandria UniversityIbrahimia, AlexandriaEgypt
  4. 4.Department of Chemistry, Faculty of ScienceTanta UniversityTantaEgypt
  5. 5.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  6. 6.Department of Medicinal Chemistry, Faculty of PharmacyMansoura UniversityMansouraEgypt

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