Electronic structure of mesoionic compounds. The classification problem
Mesoionic compounds are conventionally categorized into two types based on the primary origin of electrons within the conjugated system, specifically determined by the arrangement of heteroatoms in the five-membered ring. An examination of diverse mesoionic compounds has been undertaken to address t...
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| Format: | Article |
| Language: | English |
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V. N. Karazin Kharkiv National University
2024-06-01
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| Series: | Вісник Харківського національного університету: Серія xімія |
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| Online Access: | https://periodicals.karazin.ua/chemistry/article/view/24532 |
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| author | Mariia Kyrpa Sergiy Kovalenko Volodymyr Ivanov |
| author_facet | Mariia Kyrpa Sergiy Kovalenko Volodymyr Ivanov |
| author_sort | Mariia Kyrpa |
| collection | DOAJ |
| description | Mesoionic compounds are conventionally categorized into two types based on the primary origin of electrons within the conjugated system, specifically determined by the arrangement of heteroatoms in the five-membered ring. An examination of diverse mesoionic compounds has been undertaken to address the pivotal query surrounding their classification: does the primary origin of electrons hold significance, and does this criterion demarcate a definitive boundary between the two types of compounds? To comprehensively address this issue, the DFT calculations were performed for a set of mesoionic molecules. The electronic properties of the molecules were studied within the frameworks of quantum theory of atoms in molecules (QTAIM) and the Nuclear Independent Chemical Shift (NICS).
To comprehend the topological distinctions among representatives of the two types, we describe a set of indices designed to characterize the spatial distribution of electronic parameters within the molecular frameworks. The results obtained show that the existing classification is to a certain extent justified, with the main distinguishing factor between the two types being the nature of the distribution of the resulting ellipticities of bonds in five-membered ring and the structure of the molecular orbitals. At the same time, based on NICS calculations we concluded that both classes are not characterized by pronounced aromaticity of the mesoionic ring for the selected set of molecules. |
| format | Article |
| id | doaj-art-78bd60bd56f94856926907a05d92eedb |
| institution | Kabale University |
| issn | 2220-637X 2220-6396 |
| language | English |
| publishDate | 2024-06-01 |
| publisher | V. N. Karazin Kharkiv National University |
| record_format | Article |
| series | Вісник Харківського національного університету: Серія xімія |
| spelling | doaj-art-78bd60bd56f94856926907a05d92eedb2025-01-10T11:27:20ZengV. N. Karazin Kharkiv National UniversityВісник Харківського національного університету: Серія xімія2220-637X2220-63962024-06-0142384410.26565/2220-637X-2024-42-0424532Electronic structure of mesoionic compounds. The classification problemMariia Kyrpa0Sergiy Kovalenko1Volodymyr Ivanov2V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61022, UkraineV. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61022, UkraineV. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61022, UkraineMesoionic compounds are conventionally categorized into two types based on the primary origin of electrons within the conjugated system, specifically determined by the arrangement of heteroatoms in the five-membered ring. An examination of diverse mesoionic compounds has been undertaken to address the pivotal query surrounding their classification: does the primary origin of electrons hold significance, and does this criterion demarcate a definitive boundary between the two types of compounds? To comprehensively address this issue, the DFT calculations were performed for a set of mesoionic molecules. The electronic properties of the molecules were studied within the frameworks of quantum theory of atoms in molecules (QTAIM) and the Nuclear Independent Chemical Shift (NICS). To comprehend the topological distinctions among representatives of the two types, we describe a set of indices designed to characterize the spatial distribution of electronic parameters within the molecular frameworks. The results obtained show that the existing classification is to a certain extent justified, with the main distinguishing factor between the two types being the nature of the distribution of the resulting ellipticities of bonds in five-membered ring and the structure of the molecular orbitals. At the same time, based on NICS calculations we concluded that both classes are not characterized by pronounced aromaticity of the mesoionic ring for the selected set of molecules.https://periodicals.karazin.ua/chemistry/article/view/24532mesoionic compoundsdensity functional theoryquantum theory of atoms in moleculesnuclear independent chemical shifts |
| spellingShingle | Mariia Kyrpa Sergiy Kovalenko Volodymyr Ivanov Electronic structure of mesoionic compounds. The classification problem Вісник Харківського національного університету: Серія xімія mesoionic compounds density functional theory quantum theory of atoms in molecules nuclear independent chemical shifts |
| title | Electronic structure of mesoionic compounds. The classification problem |
| title_full | Electronic structure of mesoionic compounds. The classification problem |
| title_fullStr | Electronic structure of mesoionic compounds. The classification problem |
| title_full_unstemmed | Electronic structure of mesoionic compounds. The classification problem |
| title_short | Electronic structure of mesoionic compounds. The classification problem |
| title_sort | electronic structure of mesoionic compounds the classification problem |
| topic | mesoionic compounds density functional theory quantum theory of atoms in molecules nuclear independent chemical shifts |
| url | https://periodicals.karazin.ua/chemistry/article/view/24532 |
| work_keys_str_mv | AT mariiakyrpa electronicstructureofmesoioniccompoundstheclassificationproblem AT sergiykovalenko electronicstructureofmesoioniccompoundstheclassificationproblem AT volodymyrivanov electronicstructureofmesoioniccompoundstheclassificationproblem |