CaltechAUTHORS
Published June 1, 2018 | Version Supplemental Material
Journal Article Open

Reaction Electronic Flux Perspective on the Mechanism of the Zimmerman Di-π-methane Rearrangement

Creators

  • 1. ROR icon Pontificia Universidad Católica de Chile
  • 2. ROR icon California Institute of Technology
  • 3. ROR icon Universidad Bernardo O'Higgins
  • 4. ROR icon Andrés Bello University
  • 5. ROR icon Metropolitan University of Technology

Abstract

The reaction electronic flux (REF) offers a powerful tool in the analysis of reaction mechanisms. Noteworthy, the relationship between aromaticity and REF can eventually reveal subtle electronic events associated with reactivity in aromatic systems. In this work, this relationship was studied for the triplet Zimmerman di-π-methane rearrangement. The aromaticity loss and gain taking place during the reaction is well acquainted by the REF, thus shedding light on the electronic nature of reactions involving dibenzobarrelenes.

Additional Information

© 2018 American Chemical Society. Received: February 23, 2018; Published: February 27, 2018; Publication Date (Web): February 27, 2018. The authors acknowledge the FONDECYT Grants No. 1140341, No. 1140343, and No. 1170837. N.V.-E. acknowledges the Ph.D. fellowship from CONICYT. We are indebted to Prof. Dr. Rainer Herges for kindly providing us a copy of the ACID software package. The authors declare no competing financial interest.

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Supplemental Material - jo8b00499_si_001.pdf

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jo8b00499_si_001.pdf

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Additional details

Identifiers

Eprint ID
85356
DOI
10.1021/acs.joc.8b00499
Resolver ID
CaltechAUTHORS:20180319-125008328

Related works

Describes
10.1021/acs.joc.8b00499 (DOI)

Funding

Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)
1140341
Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)
1140343
Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)
1170837
Comisión Nacional de Investigación Científica y Tecnológica (CONICYT)

Dates

Created
2018-03-26
Created from EPrint's datestamp field
Updated
2021-11-15
Created from EPrint's last_modified field