Theoretical study of the diels-alder reactions between singlet ( 1Δg) oxygen and acenes

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)7509-7518
Journal / PublicationJournal of Physical Chemistry A
Volume109
Issue number33
Publication statusPublished - 25 Aug 2005
Externally publishedYes

Abstract

The G3(MP2) method has been employed to study the 1,4-addition reactions between singlet oxygen and five acenes, including benzene, naphthalene, anthrecene, tetracene, and pentacene. In all, nine pathways between O 2 and the five acenes have been investigated. Our calculated results indicate that all nine pathways are concerted and exothermic and that the most reactive sites on the acenes are the center ring's meso-carbons. In addition, reactivity increases along the series benzene <naphthalene <anthrecene <tetracene <pentacene. This trend is identical to that of aromaticity for the five acenes. A correlation between reactivity and aromaticity is briefly rationalized with natural bond orbital (NBO) analysis and frontier molecular orbital (FMO) analysis. Furthermore, some experimental kinetics data from the literature supporting the calculated results are cited. © 2005 American Chemical Society.

Citation Format(s)

Theoretical study of the diels-alder reactions between singlet ( 1Δg) oxygen and acenes. / Chien, Siu-Hung; Cheng, Mei-Fun; Lau, Kai-Chung et al.

In: Journal of Physical Chemistry A, Vol. 109, No. 33, 25.08.2005, p. 7509-7518.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review