Reactions in Nitroimidazole and Methylnitroimidazole Triggered by Low-Energy (0-8 eV) Electrons.

Abstract

Low-energy electrons (0-8 eV) effectively decompose 4-nitroimidazole (4NI) and the two methylated isomers 1-methyl-5-nitroimidazole and 1-methyl-4-nitroimidazole via dissociative electron attachment (DEA). The involved unimolecular decompositions range from simple bond cleavages (loss of H(•), formation of NO2(-)) to complex reactions possibly leading to a complete degradation of the target molecule (formation of CN(-), etc.). At energies below 2 eV, the entire rich chemistry induced by DEA is completely quenched by methylation, as demonstrated in a previous communication (Tanzer, K.; Feketeová, L.; Puschnigg, B.; Scheier, P.; Illenberger. E.; Denifl, S. Angew. Chem., Int. Ed. 2014, 53, 12240). The observation that in 4NI neutral radicals and radical anions are formed via DEA at high efficiency already at threshold (0 eV) may have significant implications for the development of nitroimidazole-based radiosensitizers in tumor radiation therapy.

• Authors: Katrin Tanzer, Linda Feketeová, Benjamin Puschnigg, Paul Scheier, Eugen Illenberger, Stephan Denifl
• Journal: The journal of physical chemistry. A (J Phys Chem A) Vol. 119 Issue 25 Pg. 6668-75 (Jun 25 2015) ISSN: 1520-5215 [Electronic] United States
• PMID: 26020684 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anions
• Nitroimidazoles
• Radiation-Sensitizing Agents
• Hydroxyl Radical
• Hydrogen
• 4-nitroimidazole

Topics

• Anions (chemistry)
• Electrons
• Hydrogen (chemistry)
• Hydroxyl Radical (chemistry)
• Molecular Structure
• Nitroimidazoles (chemistry)
• Radiation-Sensitizing Agents (chemistry)
• Spectrum Analysis