Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties
In this work, we synthesized two new <i>s</i>-triazine incorporates pyrazole/piperidine/aniline moieties. Molecular structure investigations in the light of X-ray crystallography combined with Hirshfeld and DFT calculations were presented. Intermolecular interactions controlling the mole...
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MDPI AG
2021-12-01
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| author | Ihab Shawish Saied M. Soliman Matti Haukka Ali Aldalbahi Assem Barakat Ayman El-Faham |
| author_facet | Ihab Shawish Saied M. Soliman Matti Haukka Ali Aldalbahi Assem Barakat Ayman El-Faham |
| author_sort | Ihab Shawish |
| collection | DOAJ |
| description | In this work, we synthesized two new <i>s</i>-triazine incorporates pyrazole/piperidine/aniline moieties. Molecular structure investigations in the light of X-ray crystallography combined with Hirshfeld and DFT calculations were presented. Intermolecular interactions controlling the molecular packing of 4-(3,5-dimethyl-1<i>H</i>-pyrazol-1-yl)-<i>N</i>-phenyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; <b>5a</b> and <i>N</i>-(4-bromophenyl)-4-(3,5-dimethyl-1<i>H</i>-pyrazol-1-yl)-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; <b>5b</b> were analyzed using Hirshfeld calculations. The most dominant interactions are the H...H, N...H and H...C contacts in both compounds. The N...H and H...C interactions in <b>5a</b> and the N...H, Br...H and H...H interactions in <b>5b</b> are the most important. In addition, DFT calculations were used to compute the molecular structures of <b>5a</b> and <b>5b</b>; then, their electronic properties, as well as the <sup>1</sup>H- and <sup>13</sup>C-NMR spectra, were predicted. Both compounds are polar where <b>5a</b> (1.018 Debye) has lower dipole moment than <b>5b</b> (4.249 Debye). The NMR chemical shifts were calculated and very good correlations between the calculated and experimental data were obtained (R<sup>2</sup> = 0.938–0.997). |
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| series | Crystals |
| spelling | doaj.art-06da2723e3c4452d99b30e39a02b5d082023-11-23T07:48:34ZengMDPI AGCrystals2073-43522021-12-011112150010.3390/cryst11121500Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline MoietiesIhab Shawish0Saied M. Soliman1Matti Haukka2Ali Aldalbahi3Assem Barakat4Ayman El-Faham5Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, 40014 Jyväskylä, FinlandDepartment 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 ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptIn this work, we synthesized two new <i>s</i>-triazine incorporates pyrazole/piperidine/aniline moieties. Molecular structure investigations in the light of X-ray crystallography combined with Hirshfeld and DFT calculations were presented. Intermolecular interactions controlling the molecular packing of 4-(3,5-dimethyl-1<i>H</i>-pyrazol-1-yl)-<i>N</i>-phenyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; <b>5a</b> and <i>N</i>-(4-bromophenyl)-4-(3,5-dimethyl-1<i>H</i>-pyrazol-1-yl)-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; <b>5b</b> were analyzed using Hirshfeld calculations. The most dominant interactions are the H...H, N...H and H...C contacts in both compounds. The N...H and H...C interactions in <b>5a</b> and the N...H, Br...H and H...H interactions in <b>5b</b> are the most important. In addition, DFT calculations were used to compute the molecular structures of <b>5a</b> and <b>5b</b>; then, their electronic properties, as well as the <sup>1</sup>H- and <sup>13</sup>C-NMR spectra, were predicted. Both compounds are polar where <b>5a</b> (1.018 Debye) has lower dipole moment than <b>5b</b> (4.249 Debye). The NMR chemical shifts were calculated and very good correlations between the calculated and experimental data were obtained (R<sup>2</sup> = 0.938–0.997).https://www.mdpi.com/2073-4352/11/12/1500<i>s</i>-triazinepyrazolehydrazino-<i>s</i>-triazineHirshfeld calculations |
| spellingShingle | Ihab Shawish Saied M. Soliman Matti Haukka Ali Aldalbahi Assem Barakat Ayman El-Faham Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties Crystals <i>s</i>-triazine pyrazole hydrazino-<i>s</i>-triazine Hirshfeld calculations |
| title | Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties |
| title_full | Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties |
| title_fullStr | Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties |
| title_full_unstemmed | Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties |
| title_short | Synthesis, and Molecular Structure Investigations of a New <em>s</em>-Triazine Derivatives Incorporating Pyrazole/Piperidine/Aniline Moieties |
| title_sort | synthesis and molecular structure investigations of a new em s em triazine derivatives incorporating pyrazole piperidine aniline moieties |
| topic | <i>s</i>-triazine pyrazole hydrazino-<i>s</i>-triazine Hirshfeld calculations |
| url | https://www.mdpi.com/2073-4352/11/12/1500 |
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