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  4. Structure-Correlation Principles Connecting Ground State Properties and Reaction Barrier Heights for the Cope Rearrangement of Semibullvalenes
 
research article

Structure-Correlation Principles Connecting Ground State Properties and Reaction Barrier Heights for the Cope Rearrangement of Semibullvalenes

Jana, Daniel  
•
Wodrich, Matthew  
•
Corminboeuf, Clemence  
2012
The Journal of Organic Chemistry

A direct relationship exists between the properties of substituted semibullvalenes and their Cope rearrangement activation barrier. This unique correlation not only enables the determination of kinetic data from ground state information, but also provides a rationalization for the extent to which ground state properties are altered with respect to their "normal" values (i.e., that of their localized Lewis structure). Examination of electron density distribution, geometrical parameters, and J-coupling constant differences between canonical and Lewis structures deliver quantitative evidence for the structure correlation principle.

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Type
research article
DOI
10.1021/jo202606v
Web of Science ID

WOS:000300915900052

Author(s)
Jana, Daniel  
Wodrich, Matthew  
Corminboeuf, Clemence  
Date Issued

2012

Publisher

American Chemical Society

Published in
The Journal of Organic Chemistry
Volume

77

Issue

5

Start page

2548

End page

2552

Subjects

Structure-Correlation Principles

•

Cope rearrangements

•

density functional theory

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCMD  
Available on Infoscience
February 9, 2012
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/77617
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