Off the Beaten Path: Almost Clean Formation of Indene from the ortho-Benzyne + Allyl Reaction.
- McCabe MN Laboratory for Astrophysics, Leiden Observatory, Leiden University, P.O. Box 9513, 2300 RA Leiden, The Netherlands.
- Hemberger P Laboratory for Synchrotron Radiation and Femtochemistry, Paul Scherrer Institute, 5232 Villigen, Switzerland.
- Reusch E Institute of Physical and Theoretical Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
- Bodi A Laboratory for Synchrotron Radiation and Femtochemistry, Paul Scherrer Institute, 5232 Villigen, Switzerland.
- Bouwman J Laboratory for Astrophysics, Leiden Observatory, Leiden University, P.O. Box 9513, 2300 RA Leiden, The Netherlands.
- 2020-03-24
Published in:
- The journal of physical chemistry letters. - 2020
English
Polycyclic aromatic hydrocarbons (PAHs) play an important role in chemistry both in the terrestrial setting and in the interstellar medium. Various, albeit often inefficient, chemical mechanisms have been proposed to explain PAH formation, but few yield polycyclic hydrocarbons cleanly. Alternative and quite promising pathways have been suggested to address these shortcomings with key starting reactants including resonance stabilized radicals (RSRs) and o-benzyne. Here we report on a combined experimental and theoretical study of the reaction allyl + o-benzyne. Indene was found to be the primary product and statistical modeling predicts only 0.1% phenylallene and 0.1% 3-phenyl-1-propyne as side products. The quantitative and likely barrierless formation of indene yields important insights into the role resonance stabilized radicals play in the formation of polycyclic hydrocarbons.
- Language
-
- English
- Open access status
- hybrid
- Identifiers
-
- DOI 10.1021/acs.jpclett.0c00374
- PMID 32202794
- Persistent URL
- https://sonar.ch/global/documents/41083
Statistics
Document views: 26
File downloads:
- Full-text: 0