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Issue 14, 2014
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Complementarity of reaction force and electron localization function analyses of asynchronicity in bond formation in Diels–Alder reactions

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Abstract

We have computationally compared three Diels–Alder cycloadditions involving cyclopentadiene and substituted ethylenes; one of the reactions is synchronous, while the others are slightly or highly asynchronous. Synchronicity and weak asynchronicity are characterized by the reaction force constant κ(ξ) having just a single minimum in the transition region along the intrinsic reaction coordinate ξ, while for high asynchronicity κ(ξ) has a negative maximum with minima on both sides. The electron localization function (ELF) shows that the features of κ(ξ) can be directly related to the formation of the new C–C bonds between the diene and the dienophile. There is thus a striking complementarity between κ(ξ) and ELF; κ(ξ) identifies the key points along ξ and ELF describes what is happening at those points.

Graphical abstract: Complementarity of reaction force and electron localization function analyses of asynchronicity in bond formation in Diels–Alder reactions

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Article information


Submitted
11 Nov 2013
Accepted
06 Feb 2014
First published
06 Feb 2014

Phys. Chem. Chem. Phys., 2014,16, 6726-6734
Article type
Paper

Complementarity of reaction force and electron localization function analyses of asynchronicity in bond formation in Diels–Alder reactions

D. Yepes, J. S. Murray, P. Pérez, L. R. Domingo, P. Politzer and P. Jaque, Phys. Chem. Chem. Phys., 2014, 16, 6726
DOI: 10.1039/C3CP54766C

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