Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide
4-Bromobenzamidrazone reacts with cyclopentanone giving 3-(4-bromophenyl)-5-(4-peroxobutyl)-1,2,4-triazole, which precipitated as pale-yellow crystals during the reaction. The intermolecular noncovalent interactions Br···Br in the single-crystal XRD structure of the peroxo compound were studied theo...
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MDPI AG
2020-04-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/12/4/637 |
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| author | Dmitrii S. Bolotin Mikhail V. Il’in Vitalii V. Suslonov Alexander S. Novikov |
| author_facet | Dmitrii S. Bolotin Mikhail V. Il’in Vitalii V. Suslonov Alexander S. Novikov |
| author_sort | Dmitrii S. Bolotin |
| collection | DOAJ |
| description | 4-Bromobenzamidrazone reacts with cyclopentanone giving 3-(4-bromophenyl)-5-(4-peroxobutyl)-1,2,4-triazole, which precipitated as pale-yellow crystals during the reaction. The intermolecular noncovalent interactions Br···Br in the single-crystal XRD structure of the peroxo compound were studied theoretically using quantum chemical calculations (ωB97XD/x2c-TZVPPall) and quantum theory of atoms in molecules (QTAIM) analysis. These attractive intermolecular noncovalent interactions Br···Br is type I halogen···halogen contacts and their estimated energy is 2.2–2.5 kcal/mol. These weak interactions are suggested to be one of the driving forces (albeit surely not the main one) for crystallization of the peroxo compound during the reaction and thus its stabilization in the solid state. |
| first_indexed | 2024-03-10T20:25:43Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-10T20:25:43Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-fef147f89c4b433489b5be09dd2ca1e12023-11-19T21:53:07ZengMDPI AGSymmetry2073-89942020-04-0112463710.3390/sym12040637Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary PeroxideDmitrii S. Bolotin0Mikhail V. Il’in1Vitalii V. Suslonov2Alexander S. Novikov3Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, RussiaInstitute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, RussiaCenter for X-ray Diffraction Studies, Saint Petersburg State University, Universitetskii Pr., 26, Saint Petersburg 198504, RussiaInstitute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, Russia4-Bromobenzamidrazone reacts with cyclopentanone giving 3-(4-bromophenyl)-5-(4-peroxobutyl)-1,2,4-triazole, which precipitated as pale-yellow crystals during the reaction. The intermolecular noncovalent interactions Br···Br in the single-crystal XRD structure of the peroxo compound were studied theoretically using quantum chemical calculations (ωB97XD/x2c-TZVPPall) and quantum theory of atoms in molecules (QTAIM) analysis. These attractive intermolecular noncovalent interactions Br···Br is type I halogen···halogen contacts and their estimated energy is 2.2–2.5 kcal/mol. These weak interactions are suggested to be one of the driving forces (albeit surely not the main one) for crystallization of the peroxo compound during the reaction and thus its stabilization in the solid state.https://www.mdpi.com/2073-8994/12/4/637organic peroxidetriazoleDFTQTAIMnoncovalent interactionshalogen bonding |
| spellingShingle | Dmitrii S. Bolotin Mikhail V. Il’in Vitalii V. Suslonov Alexander S. Novikov Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide Symmetry organic peroxide triazole DFT QTAIM noncovalent interactions halogen bonding |
| title | Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide |
| title_full | Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide |
| title_fullStr | Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide |
| title_full_unstemmed | Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide |
| title_short | Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide |
| title_sort | symmetrical noncovalent interactions br···br observed in crystal structure of exotic primary peroxide |
| topic | organic peroxide triazole DFT QTAIM noncovalent interactions halogen bonding |
| url | https://www.mdpi.com/2073-8994/12/4/637 |
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