Jump to main content
Jump to site search

Issue 27, 2018
Previous Article Next Article

Dissociative electron attachment induced ring opening in five-membered heterocyclic compounds

Author affiliations

Abstract

Five-membered heterocyclic structures, which exist widely in biological systems and play an active role in various biochemical processes, have been studied extensively from a fundamental perspective. Here, the fragmentation patterns of isoxazole, a representative five-membered heterocycle, upon dissociative electron attachment (DEA) were examined carefully by comparing isoxazole's products with those of its methylated derivatives. It was found that the most dominant DEA pathway occurs through the loss of hydrogen at C(3), which leads to ring opening by O–N bond cleavage at an energy of ∼1.5 eV. The ring opening was investigated further for DEA to other related five-membered ring compounds, i.e., oxazole and thiazole. The DEA-induced hydrogen loss was much less pronounced or quenched completely in these two compounds and simultaneous ring-opening behavior was not detected. This observation is of special interest to applied fields, for example, the pharmaceutical industry, because several drugs that contain isoxazole substructures exhibit extensive ring opening during biotransformation.

Graphical abstract: Dissociative electron attachment induced ring opening in five-membered heterocyclic compounds

Back to tab navigation

Publication details

The article was received on 28 Apr 2018, accepted on 17 Jun 2018 and first published on 19 Jun 2018


Article type: Paper
DOI: 10.1039/C8CP02718H
Citation: Phys. Chem. Chem. Phys., 2018,20, 18271-18278
  •   Request permissions

    Dissociative electron attachment induced ring opening in five-membered heterocyclic compounds

    Z. Li, I. Carmichael and S. Ptasińska, Phys. Chem. Chem. Phys., 2018, 20, 18271
    DOI: 10.1039/C8CP02718H

Search articles by author

Spotlight

Advertisements