NDLI: A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes

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A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes

Content Provider	Royal Society of Chemistry (RSC)
Author	Darù, Andrea Domingo, Luis R. Ríos-Gutiérrez, Mar Tejero, Tomás Merino, Pedro
Copyright Year	2017
Abstract	The [3 + 2] cycloaddition (32CA) reaction between nitrones and ketenes has been studied within the Molecular Electron Density Theory (MEDT) at the Density Functional Theory (DFT) MPWB1K/6-311G(d,p) computational level. Analysis of the conceptual DFT reactivity indices allows the explanation of the reactivity, and the chemo- and regioselectivity experimentally observed. The particular mechanism of this 32CA reaction involving low electrophilic ketenes has been elucidated by using a bonding evolution theory (BET) study. It is determined that this reaction takes place in one kinetic step only but in a non-concerted manner since two stages are clearly identified. Indeed, the formation of the second C–O bond begins when the first O–C bond is already formed. This study has also been applied to predict the reactivity of nitrones with highly electrophilic ketenes. Interestingly, this study predicts a switch to a two-step mechanism due to the higher polar character of this zw-type 32CA reaction. In both cases, BET supports the non-concerted nature of the 32CA reactions between nitrones and ketenes.
Starting Page	1618
Ending Page	1627
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	15
Issue Number	7
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c6ob02768g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	BET Cycloaddition Regioselectivity Chemical bond Density functional theory Electrophile
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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