Publicação
Identification of carbonium and carbenium ions by QTAIM
| Resumo: | The Gassman-Fentiman tool of increasing electron demand was used to identify carbonium and carbenium ions. Nonetheless, due to its ambiguous understanding, it was pivot of a historical dispute. We applied the Quantum Theory of Atoms in Molecules (QTAIM) metodology to characterize the carbonium and carbenium ions on an easier and more effective way. By comparing selected topological information of reference carbenium ions the QTAIM metodology can be used to evaluate whether a carbocation is classical or not. In addition, it is possible to rank a set of carbonium ions in order of their corresponding σ or π delocalization. There are few differences between our QTAIM-based model and Gassman-Fentiman tool. Unlike Gassman-Fentiman tool results, 7-anisyl-7-norbornenyl and 2-anisyl-2-norbornyl cations are non-classical, although they are the least nonclassical ions in their corresponding set of studied cations. |
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| Autores principais: | Firme, Caio Lima |
| Outros Autores: | Antunes, Octavio Augusto Ceva; Esteves, Pierre Mothé |
| Assunto: | Norbornyl cation Norbornenyl cation QTAIM Carbonium ion Carbenium ion |
| Ano: | 2021 |
| País: | Brasil |
| Tipo de documento: | artigo |
| Tipo de acesso: | unknown |
| Instituição associada: | IBICT |
| Idioma: | inglês |
| Origem: | Oasisbr |
| Resumo: | The Gassman-Fentiman tool of increasing electron demand was used to identify carbonium and carbenium ions. Nonetheless, due to its ambiguous understanding, it was pivot of a historical dispute. We applied the Quantum Theory of Atoms in Molecules (QTAIM) metodology to characterize the carbonium and carbenium ions on an easier and more effective way. By comparing selected topological information of reference carbenium ions the QTAIM metodology can be used to evaluate whether a carbocation is classical or not. In addition, it is possible to rank a set of carbonium ions in order of their corresponding σ or π delocalization. There are few differences between our QTAIM-based model and Gassman-Fentiman tool. Unlike Gassman-Fentiman tool results, 7-anisyl-7-norbornenyl and 2-anisyl-2-norbornyl cations are non-classical, although they are the least nonclassical ions in their corresponding set of studied cations. |
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