Theoretical secondary deuterium and primary C-14 kinetic isotope effects have been calculated for concerted and stepwise Diels-Alder reactions of butadiene with ethylene and acrolein. Comparisons between theory and experiment on substituted cases give definitive evidence for the mechanism and transition state geometries of the Diels-Alder reactions. Five levels of ab initio theory up to MCSCF/6-31G* are used for isotope effect calculations. The isotope effects for the retro-Diels-Alder reaction of ethanoanthracene are calculated and compared directly to experiment.

THEORETICAL SECONDARY KINETIC ISOTOPE EFFECTS AND THE INTERPRETATION OF TRANSITION-STATE GEOMETRIES .2. THE DIELS-ALDER REACTION TRANSITION-STATE GEOMETRY / J. STORER, L. RAIMONDI, K. HOUK. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 116:21(1994), pp. 9675-9683.

THEORETICAL SECONDARY KINETIC ISOTOPE EFFECTS AND THE INTERPRETATION OF TRANSITION-STATE GEOMETRIES .2. THE DIELS-ALDER REACTION TRANSITION-STATE GEOMETRY

L. RAIMONDI
Secondo
;
1994

Abstract

Theoretical secondary deuterium and primary C-14 kinetic isotope effects have been calculated for concerted and stepwise Diels-Alder reactions of butadiene with ethylene and acrolein. Comparisons between theory and experiment on substituted cases give definitive evidence for the mechanism and transition state geometries of the Diels-Alder reactions. Five levels of ab initio theory up to MCSCF/6-31G* are used for isotope effect calculations. The isotope effects for the retro-Diels-Alder reaction of ethanoanthracene are calculated and compared directly to experiment.
Settore CHIM/06 - Chimica Organica
Settore CHIM/02 - Chimica Fisica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187324
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 115
  • ???jsp.display-item.citation.isi??? 105
social impact