Theoretical investigation of cheletroptic decarbonylation reactions

Chin Hung Lai, Elise Y. Li, Kew Yu Chen, Tahsin J. Chow, Pi Tai Chou

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

In this study, B3LYP is used to calculate the decarbonylation reactions of the bicyclo-[2.2.1]hepta-2,5-dien-7-one (7-norbornadienone, 1) and its related extended fused aromatic analogues 2-5. On the basis of our results, all of the reactions tend to proceed synchronously to expel CO, forming the corresponding aromatic hydrocarbons. It is found that the more exothermic the reaction is, the less of a reaction barrier it needs to overcome. Moreover, upon a decrease of the reaction exothermicity, the structure of the transition state is farther away from the reactant, and the reaction barrier increases. The results agree well with the Hammond postulate as well as the Bell-Evans-Polanyi principle. Studies predict an activation energy of 27.83 kcal/mol for 5, so that the production of pentacene from compound 5 might proceed at elevated temperatures such as 400 K.

Original languageEnglish
Pages (from-to)1078-1084
Number of pages7
JournalJournal of Chemical Theory and Computation
Volume2
Issue number4
DOIs
Publication statusPublished - 2006 Dec 1

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Aromatic Hydrocarbons
Aromatic hydrocarbons
Carbon Monoxide
Activation energy
Temperature
axioms
bells
pentacene
hydrocarbons
analogs
activation energy

ASJC Scopus subject areas

  • Computer Science Applications
  • Physical and Theoretical Chemistry

Cite this

Theoretical investigation of cheletroptic decarbonylation reactions. / Lai, Chin Hung; Li, Elise Y.; Chen, Kew Yu; Chow, Tahsin J.; Chou, Pi Tai.

In: Journal of Chemical Theory and Computation, Vol. 2, No. 4, 01.12.2006, p. 1078-1084.

Research output: Contribution to journalArticle

Lai, Chin Hung ; Li, Elise Y. ; Chen, Kew Yu ; Chow, Tahsin J. ; Chou, Pi Tai. / Theoretical investigation of cheletroptic decarbonylation reactions. In: Journal of Chemical Theory and Computation. 2006 ; Vol. 2, No. 4. pp. 1078-1084.
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