The effect of electron-withdrawing groups in the fragmentation of the radical anions of benzyl phenyl ethers

Xavier Asensio, Àngels González-Lafont, Jordi Marquet, José M. Lluch, Michel Geoffroy

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

Abstract

The objective of this paper is to compare the influence of two electron-withdrawing groups (-CN and -NO2) in the fragmentation of 2-methoxy-4-nitrophenyl benzyl ether and 4-cyanophenyl benzyl ether once these species are reduced. The stability of the corresponding radical anions depends essentially on those substituents. In our design we have chosen two species that are able to attach the electron but which have each a different capacity to retain it. An experimental study is carried out by EPR spectroscopy to analyze the different electronic nature of the generated radical anions. In addition, electronic structure calculations at the DFT level of theory have been performed to study those radical anions and their fragmentation pathways. The thermodynamics and kinetics of the two fragmentations are discussed and compared in detail. © 2009 Elsevier B.V. All rights reserved.
Original languageEnglish
Pages (from-to)228-235
JournalJournal of Molecular Structure: THEOCHEM
Volume913
Issue number1-3
DOIs
Publication statusPublished - 15 Nov 2009

Keywords

  • Benzyl phenyl ethers
  • DFT calculations
  • Fragmentation of radical anions
  • Hyperfine coupling constants

Fingerprint

Dive into the research topics of 'The effect of electron-withdrawing groups in the fragmentation of the radical anions of benzyl phenyl ethers'. Together they form a unique fingerprint.

Cite this