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Molecules 2019, 24(3), 462; https://doi.org/10.3390/molecules24030462

Understanding the Molecular Mechanism of the Rearrangement of Internal Nitronic Ester into Nitronorbornene in Light of the MEDT Study

Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155 Kraków, Poland
Academic Editor: Luis R. Domingo
Received: 18 December 2018 / Revised: 21 January 2019 / Accepted: 24 January 2019 / Published: 28 January 2019
(This article belongs to the Special Issue The Molecular Electron Density Theory in Organic Chemistry)
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Abstract

The characterization of the structure of nitronic esters and their rearrangement into nitronorbornene reactions has been analyzed within the Molecular Electron Density Theory (MEDT) using Density Functional Theory (DFT) calculations at the B3LYP/6-31G(d) computational level. Quantum-chemical calculations indicate that this rearrangement takes place according to a one-step mechanism. The sequential bonding changes received from the Bonding Evolution Theory (BET) analysis of the rearrangement of internal nitronic ester to nitronorbornene allowed us to distinguish seven different phases. This fact clearly contradicts the formerly-proposed concerted pericyclic mechanism. View Full-Text
Keywords: molecular electron density theory; bonding evolution theory; electron localization function; molecular mechanism; Diels–Alder reaction; nitro compounds molecular electron density theory; bonding evolution theory; electron localization function; molecular mechanism; Diels–Alder reaction; nitro compounds
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kącka-Zych, A. Understanding the Molecular Mechanism of the Rearrangement of Internal Nitronic Ester into Nitronorbornene in Light of the MEDT Study. Molecules 2019, 24, 462.

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