Dissociation of gas-phase anisole induced by low-energy electron interactions: understanding patterns of aromatic bond cleavage

Finley, Jacob; Kharchilava, Giorgi; Carmichael, Ian; Chakraborty, Dipayan; Ptasinska, Sylwia

doi:10.1088/1402-4896/adb8a9

Title: Dissociation of gas-phase anisole induced by low-energy electron interactions: understanding patterns of aromatic bond cleavage

Journal Article · 03 March 2025 · Physica Scripta

DOI: https://doi.org/10.1088/1402-4896/adb8a9 · OSTI ID:2526665

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Abstract In view of elucidating the fragmentation patterns of aromatic systems induced by low-energy electron interactions, dissociative electron attachment (DEA) to gas-phase anisole was performed. Anionic fragments resulting from this DEA process were detected by a quadrupole mass spectrometer, and ion yields of those fragments as a function of incident electron energy were rendered. Our study showed the formation of CH ₃ ⁻ , HCC ⁻ , and OCH ₃ ⁻ fragments, suggesting that various dissociation channels proceed out of DEA to anisole. We employed density functional theory to compute thermodynamic threshold energies for each potential dissociation channel. Those theoretical calculations supported the prediction that the CH ₃ ⁻ and OCH ₃ ⁻ fragments form via mechanisms of single-bond cleavage; the HCC ⁻ fragments may form through two-, three-, or four-body dissociation channels that entail hydrogen transfers and the cleavage of multiple aromatic bonds. The experimental resonance energies that form the CH ₃ ⁻ , HCC ⁻ , and OCH ₃ ⁻ fragments were 6.0 eV, 5.8 and 9.7 eV, and 9.8 eV, respectively. Given the classification of anisole as a monosubstituted aromatic species, our results explain generalizable patterns of electron-mediated dissociation in aromatic systems.

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FC02-04ER15533

OSTI ID:: 2526665

Journal Information:: Physica Scripta, Journal Name: Physica Scripta Journal Issue: 4 Vol. 100; ISSN 0031-8949

Publisher:: IOP PublishingCopyright Statement

Country of Publication:: Sweden

Language:: English

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