Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations
The novel hydrazone-containing thieno[2,3-<i>d</i>]pyrimidine, namely, <i>N</i>′-(1,3-dioxo-1,3-dihydro-2<i>H</i>-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-3(4<i>H</i>)-yl)acetohydrazide <b>4&...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/3/384 |
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| author | Mezna Saleh Altowyan Matti Haukka Saied M. Soliman Assem Barakat Ahmed T. A. Boraei Manar Sopaih |
| author_facet | Mezna Saleh Altowyan Matti Haukka Saied M. Soliman Assem Barakat Ahmed T. A. Boraei Manar Sopaih |
| author_sort | Mezna Saleh Altowyan |
| collection | DOAJ |
| description | The novel hydrazone-containing thieno[2,3-<i>d</i>]pyrimidine, namely, <i>N</i>′-(1,3-dioxo-1,3-dihydro-2<i>H</i>-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-3(4<i>H</i>)-yl)acetohydrazide <b>4</b> was synthesized in a very good yield from the reaction of the triketoester <b>1</b> or ninhydrin <b>2</b> with the exocyclic acetohydrazide <b>3</b> in methanol. Good-quality crystals of <b>4</b> were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product <b>4</b> crystallized in the triclinic crystal system and <i>P-1</i> space group. The topology analysis of molecular packing indicated that the H…H (30.4%), O…H (22.0%) and H…C (17.0%) contacts are the most dominant intermolecular interactions in the crystal of <b>4</b>, while the O…H, N…H, H…C, N…C, O…C, C…C and O…O are the only contacts which have shorter interaction distances than the vdWs radii sum of the interacting atoms. The structure of <b>4</b> is optimized and the calculated structure showed good agreement with the experimental one. Additionally, MEP, HOMO, LUMO and the reactivity descriptors were calculated. |
| first_indexed | 2024-03-11T06:42:31Z |
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| id | doaj.art-27a7de96c62e496aa6ac936ecc768cc3 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-11T06:42:31Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-27a7de96c62e496aa6ac936ecc768cc32023-11-17T10:28:01ZengMDPI AGCrystals2073-43522023-02-0113338410.3390/cryst13030384Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational InvestigationsMezna Saleh Altowyan0Matti Haukka1Saied M. Soliman2Assem Barakat3Ahmed T. A. Boraei4Manar Sopaih5Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandChemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaChemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptChemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptThe novel hydrazone-containing thieno[2,3-<i>d</i>]pyrimidine, namely, <i>N</i>′-(1,3-dioxo-1,3-dihydro-2<i>H</i>-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-3(4<i>H</i>)-yl)acetohydrazide <b>4</b> was synthesized in a very good yield from the reaction of the triketoester <b>1</b> or ninhydrin <b>2</b> with the exocyclic acetohydrazide <b>3</b> in methanol. Good-quality crystals of <b>4</b> were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product <b>4</b> crystallized in the triclinic crystal system and <i>P-1</i> space group. The topology analysis of molecular packing indicated that the H…H (30.4%), O…H (22.0%) and H…C (17.0%) contacts are the most dominant intermolecular interactions in the crystal of <b>4</b>, while the O…H, N…H, H…C, N…C, O…C, C…C and O…O are the only contacts which have shorter interaction distances than the vdWs radii sum of the interacting atoms. The structure of <b>4</b> is optimized and the calculated structure showed good agreement with the experimental one. Additionally, MEP, HOMO, LUMO and the reactivity descriptors were calculated.https://www.mdpi.com/2073-4352/13/3/384thieno[2,3-<i>d</i>]pyrimidineninhydrinhydrazoneX-ray crystal structureHirshfeld |
| spellingShingle | Mezna Saleh Altowyan Matti Haukka Saied M. Soliman Assem Barakat Ahmed T. A. Boraei Manar Sopaih Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations Crystals thieno[2,3-<i>d</i>]pyrimidine ninhydrin hydrazone X-ray crystal structure Hirshfeld |
| title | Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations |
| title_full | Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations |
| title_fullStr | Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations |
| title_full_unstemmed | Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations |
| title_short | Synthesis of a Novel Hydrazone of Thieno[2,3-<i>d</i>]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations |
| title_sort | synthesis of a novel hydrazone of thieno 2 3 i d i pyrimidine clubbed with ninhydrin x ray crystal structure and computational investigations |
| topic | thieno[2,3-<i>d</i>]pyrimidine ninhydrin hydrazone X-ray crystal structure Hirshfeld |
| url | https://www.mdpi.com/2073-4352/13/3/384 |
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