A bonding evolution analysis for the thermal Claisen rearrangement: an experimental and theoretical exercise for testing the electron density flow
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Other documents of the author: González Navarrete, Patricio; Andres, Juan; Safont Villarreal, Vicent Sixte
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Title
A bonding evolution analysis for the thermal Claisen rearrangement: an experimental and theoretical exercise for testing the electron density flowDate
2018Publisher
Royal Society of ChemistryISSN
1463-9076; 1463-9084Bibliographic citation
GONZÁLEZ-NAVARRETE, Patricio; ANDRÉS, Juan; SAFONT, V. Sixte. A bonding evolution analysis for the thermal Claisen rearrangement: an experimental and theoretical exercise for testing the electron density flow. Physical Chemistry Chemical Physics, 2018, vol. 20, no 1, p. 535-541.Type
info:eu-repo/semantics/articleVersion
info:eu-repo/semantics/acceptedVersionSubject
Abstract
A comprehensive theoretical investigation of the thermal Claisen rearrangement
of allyl vinyl ether (AVE) to allylacetaldehyde has been carried out. We present the use of
the electron localization function (ELF) to ... [+]
A comprehensive theoretical investigation of the thermal Claisen rearrangement
of allyl vinyl ether (AVE) to allylacetaldehyde has been carried out. We present the use of
the electron localization function (ELF) to monitor the bonding evolution aspects in the
course of this thermal rearrangement and the results are compared with a photo-impulsive
process where instantaneous vibration frequencies are monitored [Phys. Chem. Chem.
Phys., 2011, 12, 5546-5555]. Our results reveal an asynchronous electron density
rearrangement inasmuch that the breaking of the C3-O bond and the formation of the C1-
C5 do not take place simultaneously. We also demonstrate how the bonding evolution
brings about the natural appearance of the curly arrows representing the electronic flow in
molecular rearrangements. This holds the key to gaining an unprecedented insight into the
mapping of the electron density flow while the bonds change throughout the reaction
progress. [-]
Is part of
Phys. Chem. Chem. Phys., 2018, Vol. 20, Issue 1.Investigation project
PrometeoII/2014/022 ; ACOMP/2015/1202 ; UJI-B2016-25 ; CTQ2015-65207-PRights
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