Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?

Luis R. Domingo, M. José Aurell, Patricia Pérez, Renato Contreras

Resultado de la investigación: Article

115 Citas (Scopus)

Resumen

The transition structures (TSs) for a series of related Diels-Alder reactions between cyclopentadiene and mono-, di-, tri-, and tetracyanoethylene derivatives have been studied with use of DFT methods at the B3LYP/6-31G* computational level. The increase of the electron-withdrawing substitution on ethylene increases the rate of these polar cycloadditions. However, the symmetric arrangement of cis and trans 1,2-di- and tetracyanoethylenes decreases the effectiveness of the substitution, which can be related to the symmetry found at the corresponding TSs. A DFT analysis of the global and local electrophilicity power of these series of cyano ethylenes provides a sound explanation about the nature of these synchronous processes. The present theoretical study is in agreement with the experimental outcomes.

Idioma originalEnglish
Páginas (desde-hasta)3884-3890
Número de páginas7
PublicaciónJournal of Organic Chemistry
Volumen68
N.º10
EstadoPublished - 16 may 2003

Huella dactilar

Discrete Fourier transforms
Ethylenes
Substitution reactions
Cyclopentanes
Cycloaddition
Acoustic waves
Derivatives
Electrons
tetracyanoethylene
ethylene

ASJC Scopus subject areas

  • Organic Chemistry

Citar esto

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title = "Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?",
abstract = "The transition structures (TSs) for a series of related Diels-Alder reactions between cyclopentadiene and mono-, di-, tri-, and tetracyanoethylene derivatives have been studied with use of DFT methods at the B3LYP/6-31G* computational level. The increase of the electron-withdrawing substitution on ethylene increases the rate of these polar cycloadditions. However, the symmetric arrangement of cis and trans 1,2-di- and tetracyanoethylenes decreases the effectiveness of the substitution, which can be related to the symmetry found at the corresponding TSs. A DFT analysis of the global and local electrophilicity power of these series of cyano ethylenes provides a sound explanation about the nature of these synchronous processes. The present theoretical study is in agreement with the experimental outcomes.",
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Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes? / Domingo, Luis R.; Aurell, M. José; Pérez, Patricia; Contreras, Renato.

En: Journal of Organic Chemistry, Vol. 68, N.º 10, 16.05.2003, p. 3884-3890.

Resultado de la investigación: Article

TY - JOUR

T1 - Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?

AU - Domingo, Luis R.

AU - Aurell, M. José

AU - Pérez, Patricia

AU - Contreras, Renato

PY - 2003/5/16

Y1 - 2003/5/16

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