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Open AccessArticle

Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium upon Formation of Their N-Oxides

1
Department of Chemistry, York University, Keele Campus, Toronto, ON MJ3 1P3, Canada
2
Department of Chemistry, University of New Hampshire, Durham, NH 03824, USA
3
Department of Chemistry and Biochemistry, University of Maryland Baltimore County, Baltimore, MD 21250, USA
4
Department of Physics and Astronomy, York University, Keele Campus, Toronto, ON MJ3 1P3, Canada
*
Authors to whom correspondence should be addressed.
Academic Editor: René Michael Koenigs
Molecules 2020, 25(20), 4767; https://doi.org/10.3390/molecules25204767
Received: 30 August 2020 / Revised: 8 October 2020 / Accepted: 12 October 2020 / Published: 16 October 2020
(This article belongs to the Special Issue Reactive Intermediates in Organic Chemistry)
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. View Full-Text
Keywords: N-methylazepine; N-Methyl-7-azanorcaradiene; N-methylpyrrole; amine N-oxides; aromaticity; antiaromaticity; DFT calculations; NICS N-methylazepine; N-Methyl-7-azanorcaradiene; N-methylpyrrole; amine N-oxides; aromaticity; antiaromaticity; DFT calculations; NICS
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MDPI and ACS Style

Fournier, R.; Green, A.R.; Greenberg, A.; Lee-Ruff, E.; Liebman, J.F.; Rágyanszki, A. Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium upon Formation of Their N-Oxides. Molecules 2020, 25, 4767.

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