Theoretical Study of the Geometry of Dibenzoazepine Analogues
The geometry of dibenzoazepine analogues—typical multifunctional drugs—was investigated to find the geometrical parameters sensitive to the substitution of the central seven-membered ring. Exploration of the crystal structure database (CSD) shows that the geometrical parameter sensitive to the subst...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/790 |
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| author | Małgorzata Szymańska Irena Majerz |
| author_facet | Małgorzata Szymańska Irena Majerz |
| author_sort | Małgorzata Szymańska |
| collection | DOAJ |
| description | The geometry of dibenzoazepine analogues—typical multifunctional drugs—was investigated to find the geometrical parameters sensitive to the substitution of the central seven-membered ring. Exploration of the crystal structure database (CSD) shows that the geometrical parameter sensitive to the substitution of the carbon atom distance of the central ring not included in the aromatic rings to the plane through the carbon atoms common for the central ring and the aromatic side rings. Presence of the double bond in the central ring was reflected in its partial aromaticity expressed by the HOMED parameter. Some derivatives of 5<i>H</i>-dibenzo[b,f]azepine with flat conformation of the central ring are characterized by mobility of the electron density comparable to the mobility in the aromatic side rings. Influence of the surrounding on the investigated compounds was confirmed by comparison of the optimized molecules and the molecules in the crystal state where the packing forces can influence the molecular geometry. |
| first_indexed | 2024-03-09T23:29:40Z |
| format | Article |
| id | doaj.art-d34a75fe7e60437baccf40e1183c7399 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:29:40Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d34a75fe7e60437baccf40e1183c73992023-11-23T17:12:38ZengMDPI AGMolecules1420-30492022-01-0127379010.3390/molecules27030790Theoretical Study of the Geometry of Dibenzoazepine AnaloguesMałgorzata Szymańska0Irena Majerz1Faculty of Pharmacy, Wroclaw Medical University, Borowska 211a, 50-556 Wroclaw, PolandFaculty of Pharmacy, Wroclaw Medical University, Borowska 211a, 50-556 Wroclaw, PolandThe geometry of dibenzoazepine analogues—typical multifunctional drugs—was investigated to find the geometrical parameters sensitive to the substitution of the central seven-membered ring. Exploration of the crystal structure database (CSD) shows that the geometrical parameter sensitive to the substitution of the carbon atom distance of the central ring not included in the aromatic rings to the plane through the carbon atoms common for the central ring and the aromatic side rings. Presence of the double bond in the central ring was reflected in its partial aromaticity expressed by the HOMED parameter. Some derivatives of 5<i>H</i>-dibenzo[b,f]azepine with flat conformation of the central ring are characterized by mobility of the electron density comparable to the mobility in the aromatic side rings. Influence of the surrounding on the investigated compounds was confirmed by comparison of the optimized molecules and the molecules in the crystal state where the packing forces can influence the molecular geometry.https://www.mdpi.com/1420-3049/27/3/7905<i>H</i>-dibenzo[b,f]azepine10,11-dihydro-5<i>H</i>-dibenzo[b,f]azepine5<i>H</i>-dibenzo[a,d][7]annulene10,11-dihydro-5<i>H</i>-dibenzo[a,d][7]annulenemolecular structurearomaticity |
| spellingShingle | Małgorzata Szymańska Irena Majerz Theoretical Study of the Geometry of Dibenzoazepine Analogues Molecules 5<i>H</i>-dibenzo[b,f]azepine 10,11-dihydro-5<i>H</i>-dibenzo[b,f]azepine 5<i>H</i>-dibenzo[a,d][7]annulene 10,11-dihydro-5<i>H</i>-dibenzo[a,d][7]annulene molecular structure aromaticity |
| title | Theoretical Study of the Geometry of Dibenzoazepine Analogues |
| title_full | Theoretical Study of the Geometry of Dibenzoazepine Analogues |
| title_fullStr | Theoretical Study of the Geometry of Dibenzoazepine Analogues |
| title_full_unstemmed | Theoretical Study of the Geometry of Dibenzoazepine Analogues |
| title_short | Theoretical Study of the Geometry of Dibenzoazepine Analogues |
| title_sort | theoretical study of the geometry of dibenzoazepine analogues |
| topic | 5<i>H</i>-dibenzo[b,f]azepine 10,11-dihydro-5<i>H</i>-dibenzo[b,f]azepine 5<i>H</i>-dibenzo[a,d][7]annulene 10,11-dihydro-5<i>H</i>-dibenzo[a,d][7]annulene molecular structure aromaticity |
| url | https://www.mdpi.com/1420-3049/27/3/790 |
| work_keys_str_mv | AT małgorzataszymanska theoreticalstudyofthegeometryofdibenzoazepineanalogues AT irenamajerz theoreticalstudyofthegeometryofdibenzoazepineanalogues |