Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium Upon Formation of Their N-Oxides
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| Název: | Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium Upon Formation of Their N-Oxides |
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| Autoři: | René Fournier, Alexa R. Green, Arthur Greenberg, Edward Lee-Ruff, Joel F. Liebman, Anita Rágyanszki |
| Zdroj: | Molecules, Vol 25, Iss 4767, p 4767 (2020) |
| Informace o vydavateli: | MDPI AG |
| Rok vydání: | 2020 |
| Sbírka: | Directory of Open Access Journals: DOAJ Articles |
| Témata: | N-methylazepine, N-Methyl-7-azanorcaradiene, N-methylpyrrole, amine N-oxides, aromaticity, antiaromaticity, Organic chemistry, QD241-441 |
| Popis: | Density functional calculations and up to five different basis sets have been applied to the exploration of the structural, enthalpy and free energy changes upon conversion of the azepine to the corresponding N-oxide. Although it is well known that azepines are typically much more stable than their 7-azanorcaradiene valence isomers, the stabilities are reversed for the corresponding N-oxides. Structural, thermochemical as well as nucleus-independent chemical shift (NICS) criteria are employed to probe the potential aromaticity, antiaromaticity and nonaromaticity of N-methylazepine, its 7-azanorcaradiene valence isomer. For the sake of comparison, analogous studies are performed on N-methylpyrrole and its N-oxide. |
| Druh dokumentu: | article in journal/newspaper |
| Jazyk: | English |
| Relation: | https://www.mdpi.com/1420-3049/25/20/4767; https://doaj.org/toc/1420-3049; https://doaj.org/article/2f2e3dfb535f46dd81b770a9847465df |
| DOI: | 10.3390/molecules25204767 |
| Dostupnost: | https://doi.org/10.3390/molecules25204767 https://doaj.org/article/2f2e3dfb535f46dd81b770a9847465df |
| Přístupové číslo: | edsbas.7ECDA953 |
| Databáze: | BASE |
Nájsť tento článok vo Web of Science | Abstrakt: | Density functional calculations and up to five different basis sets have been applied to the exploration of the structural, enthalpy and free energy changes upon conversion of the azepine to the corresponding N-oxide. Although it is well known that azepines are typically much more stable than their 7-azanorcaradiene valence isomers, the stabilities are reversed for the corresponding N-oxides. Structural, thermochemical as well as nucleus-independent chemical shift (NICS) criteria are employed to probe the potential aromaticity, antiaromaticity and nonaromaticity of N-methylazepine, its 7-azanorcaradiene valence isomer. For the sake of comparison, analogous studies are performed on N-methylpyrrole and its N-oxide. |
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| DOI: | 10.3390/molecules25204767 |