Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives
The synthesis of C<sub>2</sub>-symmetrical <i>bis</i>(<i>β</i>-enamino-pyran-2,4-dione) derivative <b>3</b> connected via 1,6-hexylene linker was reported for the first time. X-ray structures and Hirshfeld studies of the new <i>bis</i>- <...
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2021-09-01
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| author | Ahmed T. A. Boraei Matti Haukka Ahmed A. M. Sarhan Saied M. Soliman Abdullah Mohammed Al-Majid Assem Barakat |
| author_facet | Ahmed T. A. Boraei Matti Haukka Ahmed A. M. Sarhan Saied M. Soliman Abdullah Mohammed Al-Majid Assem Barakat |
| author_sort | Ahmed T. A. Boraei |
| collection | DOAJ |
| description | The synthesis of C<sub>2</sub>-symmetrical <i>bis</i>(<i>β</i>-enamino-pyran-2,4-dione) derivative <b>3</b> connected via 1,6-hexylene linker was reported for the first time. X-ray structures and Hirshfeld studies of the new <i>bis</i>- <i>β</i>-enamino-pyran-2,4-dione derivative <b>3</b> along with two structurally related pyran-2,4-dione derivatives <b>2a,b</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 <sup>1</sup>H and <sup>13</sup>C NMR spectra of the studied systems. All compounds (except <b>3</b>) are polar where <b>2a</b> (3.540 Debye) has a higher dipole moment than <b>2b</b> (2.110 Debye). The NMR chemical shifts were calculated and excellent correlations between the calculated and experimental data were obtained (R<sup>2</sup> = 0.93–0.94). |
| first_indexed | 2024-03-10T07:10:48Z |
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| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-10T07:10:48Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-9e34e68e605f42c19b5b296b9ff334d22023-11-22T15:27:56ZengMDPI AGSymmetry2073-89942021-09-01139164610.3390/sym13091646Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) DerivativesAhmed T. A. Boraei0Matti Haukka1Ahmed A. M. Sarhan2Saied M. Soliman3Abdullah Mohammed Al-Majid4Assem Barakat5Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandChemistry Department, Faculty of Science, Arish University, Al-Arish 45511, EgyptDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaThe synthesis of C<sub>2</sub>-symmetrical <i>bis</i>(<i>β</i>-enamino-pyran-2,4-dione) derivative <b>3</b> connected via 1,6-hexylene linker was reported for the first time. X-ray structures and Hirshfeld studies of the new <i>bis</i>- <i>β</i>-enamino-pyran-2,4-dione derivative <b>3</b> along with two structurally related pyran-2,4-dione derivatives <b>2a,b</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 <sup>1</sup>H and <sup>13</sup>C NMR spectra of the studied systems. All compounds (except <b>3</b>) are polar where <b>2a</b> (3.540 Debye) has a higher dipole moment than <b>2b</b> (2.110 Debye). The NMR chemical shifts were calculated and excellent correlations between the calculated and experimental data were obtained (R<sup>2</sup> = 0.93–0.94).https://www.mdpi.com/2073-8994/13/9/1646pyran-2,4-dione<i>C</i><sub>2</sub>-symmetricalHirshfeld analysisAIMDFTintramolecular hydrogen bond |
| spellingShingle | Ahmed T. A. Boraei Matti Haukka Ahmed A. M. Sarhan Saied M. Soliman Abdullah Mohammed Al-Majid Assem Barakat Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives Symmetry pyran-2,4-dione <i>C</i><sub>2</sub>-symmetrical Hirshfeld analysis AIM DFT intramolecular hydrogen bond |
| title | Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives |
| title_full | Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives |
| title_fullStr | Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives |
| title_full_unstemmed | Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives |
| title_short | Synthesis of <i>C</i><sub>2</sub>-Symmetrical <i>Bis-</i>(<i>β</i>-Enamino-Pyran-2,4-dione) Derivative Linked via 1,6-Hexylene Spacer: X-ray Crystal Structures, Hishfeld Studies and DFT Calculations of Mono- and <i>Bis-</i>(Pyran-2,4-diones) Derivatives |
| title_sort | synthesis of i c i sub 2 sub symmetrical i bis i i β i enamino pyran 2 4 dione derivative linked via 1 6 hexylene spacer x ray crystal structures hishfeld studies and dft calculations of mono and i bis i pyran 2 4 diones derivatives |
| topic | pyran-2,4-dione <i>C</i><sub>2</sub>-symmetrical Hirshfeld analysis AIM DFT intramolecular hydrogen bond |
| url | https://www.mdpi.com/2073-8994/13/9/1646 |
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