The mechanism of electrophilic addition of singlet oxygen to unsubstituted pyrrole

Nassim Zeinali, Jomana Al-Nu’airat, Zhe Zeng, Mohammednoor Altarawneh, Dan Li, Jakub Skut, Bogdan Z. Dlugogorski

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The essential role of pyrrole in comprehending the chemistry of living organisms, coal surrogates and novel drugs is indisputable. However, literature reports a few studies on its reactivity toward prominent oxidizing agents. Herein we present a comprehensive mechanistic study of oxidation of unsubstituted pyrrole with singlet oxygen (O21g) by deploying a quantum chemical framework leading to the production of succinimide, as the major products, through a Diels-Alder addition of O21g to the aromatic ring. Other products, comprising maleimide, hydroperoxide, formamide or epoxide adducts, appear to form via rather minor channels. Additionally, we determined that, the primary Diels-Alder channel encompasses a barrier of 41 kJ/mol with a fitted rate constant of k(T)=1.87×10-13 exp(-48 000/RT) cm3 molecule-1 s-1

Original languageEnglish
Title of host publication11th Asia-Pacific Conference on Combustion 2017
EditorsA.R. Masri, M. Cleary, M. Dunn, A. Kourmatzis, E. Hawkes, S. Kook, Q.N. Chan
Place of PublicationUnited States
PublisherCombustion Institute China Section
Number of pages4
ISBN (Print)9781510856462
Publication statusPublished - 2017
Externally publishedYes
Event11th Asia-Pacific Conference on Combustion, ASPACC 2017 - Sydney, Australia
Duration: 10 Dec 201714 Dec 2017


Conference11th Asia-Pacific Conference on Combustion, ASPACC 2017


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